Decahydronaphthalene derivative

ABSTRACT

The present invention discloses a decahydronaphthalene derivative represented by general formula (I): 
                 
 
a liquid crystal composition in which it is contained, and a liquid crystal device in which it is used. The novel decahydronaphthalene derivative of the present invention can be produced industrially extremely easily as shown in the examples, and by adding a small amount to a base liquid crystal, it is possible to have effects that expand the nematic phase temperature range, thereby improving its various characteristics as a nematic liquid crystal. Moreover, the novel decahydronaphthalene derivative of the present invention also has superior co-solubility with base liquid crystals generally used at present. Thus, it is suitable for various types of liquid crystal devices requiring a wide operating temperature range, and is extremely useful as a liquid crystal material.

TECHNICAL FIELD

The present invention relates to a decahydronaphthalene derivative,which is a novel liquid crystal compound, and a liquid crystalcomposition containing said derivative. This derivative is useful as aliquid crystal material for electrooptical liquid crystal display, andhas a wide temperature range in particular.

BACKGROUND ART

Liquid crystal display elements have come to be used in not only clocksand calculators, but also in various types of measuring instruments,automobile instrument panels, word processors, Personal DigitalAssistants, printers, computers and televisions. Typical examples ofliquid crystal display methods include TN (twisted nematic) types, STN(super twisted nematic) types, DS (dynamic scattering) types, GH (guesthost) types and FLC (ferroelectric liquid crystal) types. In addition,multiplex driving instead of the conventional static driving has becomethe most common type of driving method. Moreover, simple matrix types,and more recently, active matrix types, have come into practical use.

Liquid crystal materials are required to have various characteristics toaccommodate these display and driving methods. Although a widetemperature range is extremely important in nearly all cases, thisincludes that in which the nematic phase upper limit temperature(T_(N-I)) is sufficiently high, and the melting point (T_(C-N)) or thesmectic-nematic transition temperature (T_(S-N)) is sufficiently low.

In addition, co-solubility with other liquid crystal compounds andversatile liquid crystal compositions is also important. If thisco-solubility was defective, it became necessary to mix extremely manykinds of liquid crystal compounds in order to avoid the risk ofprecipitation and phase separation, making compound preparationextremely bothersome and making increased costs unavoidable.

In addition, a sufficiently low driving voltage is also an importantcharacteristic in many cases, and it is necessary for the thresholdvoltage (V_(th)) to be low in order to accomplish this.

In addition, rapid response is also an equally important characteristic,and the viscosity of the liquid crystal is required to be as low aspossible in order to accomplish this.

In addition, birefringence (Δn) is also an important characteristic.Although various values are required according to the display method, alow value is frequently required in the case of liquid crystal deviceshaving a large cell thickness for easy manufacturing.

Although an extremely large number of liquid crystal compounds have beensynthesized in the past in order to satisfy these requirements, not allof the problems were able to be solved. Thus, there is a need for aliquid crystal compound having superior characteristics with respect toeach of the above requirements.

In general, liquid crystal compounds are formed from a central skeleton(core) portion and side groups (side chains and polar groups). There arenumerous known examples of the ring structure that composes the coreportion, such as a 1,4-phenylene group (which may be substituted withfluorine) and trans-1,4-cyclohexylene group, as well as heterocyclicaromatics such as a pyridine-2,5-diyl group and pyrimidne-2,5-diylgroup, and saturated heterocyclic rings such as a dioxane-trans-1,4-diylgroup and piperidine-1,4-diyl group. However, this ring structure ispractically limited to a 1,4-phenylene group (which may be substitutedwith fluorine), trans-1,4-cyclohexylene group and a small number ofheterocyclic aromatics. However, liquid crystal compounds composed ofthese ring structures alone are currently unable to adequatelyaccommodate the characteristics required of increasingly sophisticatedliquid crystal compounds.

Since compounds containing a trans-2,6-trans-decahydronaphthalene groupare saturated rings that do not contain hetero atoms such as oxygenatoms or nitrogen atoms, in addition to being expected to demonstratesuperior stability, they are also expected to improve liquid crystalproperties. However, there have been few examples oftrans-2,6-trans-decahydronaphthalene derivatives reported thus far (W.Sucrow and H. Wolter, Chimia, 36, 460 (1982); Mol. Cryst. Liq. Cryst.,95, 63 (1983)), and hardly anything is known regarding theircharacteristics.

DISCLOSURE OF THE INVENTION

The problem to be solved by the present invention is to provide a novelliquid crystal composition in the form of a decahydronaphthalenederivative, and to provide a liquid crystal composition suitable for STNor TFT driving that uses any of these derivatives, has a wide nematicphase temperature range, has a low birefringence, and is able to bedriven at a low voltage and respond rapidly.

In order to solve the above problems, the present invention provides anovel liquid crystal compound in the form of a decahydronaphthalenederivative represented by general formula (I).

Invention 1: A compound represented by general formula (I):

(wherein, R and Z may be substituted with a halogen and represent alkylgroups or alkoxy groups having 1-16 carbon atoms, alkenyl groups having2-16 carbon atoms, alkenyloxy groups having 3-16 carbon atoms, alkylgroups having 1-12 carbon atoms substituted with an alkoxy group having1-10 carbon atoms, hydrogen atoms, fluorine atoms, chlorine atoms,trifluoromethoxy groups, difluoromethoxy groups, trifluoromethyl groups,2,2,2-trifluoroethoxy groups, cyano groups, cyanato groups, hydroxygroups or carboxy groups, m and n may be the same or different andrespectively and independently represent an integer of 0-2, m+n 3, L andM may be the same or different and respectively and independentlyrepresent —CH₂CH₂—, —CH(CH₃)CH₂—, —CH₂CH(CH₃)—, —CH₂O—, —OCH₂—, —CF₂O—,—OCF₂—, —COO—, —OCO—, —CH═CH—, —CF═CF—, —C C—, —O(CH₂)₃—, —(CH₂)₃O—,—(CH₂)₄— or a single bond, rings A and B when present may be the same ordifferent and respectively and independently represent atrans-1,4-cyclohexylene group in which one CH₂ group or more than onenon-adjacent CH₂ groups in the group may be replaced by —O— or —S—, a1,4-phenylene group in which one CH₂ group or more than one non-adjacentCH₂ groups in the group may be replaced by —N═, a 1,4-cyclohexenylenegroup, 1,4-bicyclo(2,2,2)octylene group, piperidine-1,4-diyl group,naphthalene-2,6-diyl group, trans-decahydronaphthalene-trans-2,6-diylgroup or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and althoughthese may be substituted with a cyano group or halogen, in the case m orn represents 2, at least one of the two L or M present represents asingle bond; provided that the following cases are excluded:

-   1. case in which m and n represent 0, R represents a non-substituted    alkyl group, and Z represents a non-substituted alkyl group or cyano    group;-   2. case in which either m or n represents 1, the other of m or n    represents 0, ring A or ring B when present represents a    1,4-cyclohexylene group, L or M when present represents a single    bond, R or Z bonded to a decahydronaphthalene ring represents a    non-substituted alkyl group, and R or Z bonded to a    1,4-cyclohexylene group represents a non-substituted alkyl group,    alkoxy group or alkenyloxy group;-   3. case in which either m or n represents 1, the other m or n    represents 0, ring A or ring B when present represents a    1,4-cyclohexylene group, L when present represents —OCO— or M when    present represents —COO—, R or Z bonded to a decahydronaphthalene    ring represents a non-substituted alkyl group, and R or Z bonded to    a 1,4-cyclohexylene group represents a non-substituted alkyl group    or cyano group;-   4. case in which either m or n represents 1, the other m or n    represents 0, ring A or ring B when present represents a    non-substituted 1,4-phenylene group, L when present represents —OCO—    or M when present represents —COO—, L or M when present represents a    single bond, R or Z bonded to a decahydronaphthalene ring represents    an alkyl group, and R or Z bonded to a 1,4-phenylene group    represents a non-substituted alkyl group, alkoxy group or cyano    group;-   5. case in which either m or n represents 1, the other m or n    represents 0, ring A or ring B when present represents a    non-substituted 1,4-phenylene group, L or M when present represents    a single bond, R or Z bonded to a decahydronaphthalene ring    represents a non-substituted alkoxy group, and R or Z bonded to a    1,4-phenylene group represents a non-substituted alkyl group;-   6. case in which either m or n represents 1, the other m or n    represents 0, ring A or ring B when present represents a    trans-decahydronaphthalene-trans-2,6-diyl group, L when present    represents —OCO—, M when present represents —COO— or L or M when    present represent a single bond, and R and Z represent    non-substituted alkoxy groups;-   7. case in which either m or n represents 1, the other m or n    represents 0, ring A or ring B when present represents a    non-substituted naphthalene-2,6-diyl group, L when present    represents —OCO— or M when present represents —COO—, R or Z bonded    to a decahydronaphthalene ring represents a non-substituted alkyl    group, and R or Z bonded to a naphthalene-2,6-diyl group represents    a non-substituted alkyl group, bromine atom or cyano group, or the    case in which R or Z bonded to a decahydronaphthalene ring    represents a non-substituted alkoxy group, and R or Z bonded to a    naphthalene-2,6-diyl group represents a non-substituted alkyl group    or cyano group;-   8. case in which n represents 2, m represents 0, R represents a    non-substituted alkyl group, M when present adjacent to a    decahydronaphthalene ring represents —COO—, at least one of rings B    present represents a non-substituted 1,4-phenylene group, and Z    represents a non-substituted alkyl group or bromine atom, or the    case in which at least one of rings B present represents a    pyrimidine-2,5-diyl group, and Z represents a non-substituted alkyl    group, alkoxy group or cyano group;-   9. case in which m and n represent 1, ring A represents a    trans-decahydronaphthalene-trans-2,6-diyl group or a    1,4-cyclohexylene group, ring B represents a non-substituted    1,4-phenylene group or 1,4-cyclohexylene group, L represents a    single bond, M represents —COO—, —OCO—, —CH₂O— or —OCH₂—, and R and    Z represent non-substituted alkyl groups; and,    -   applying similarly to compounds equivalent to the above using        combinations of the abbreviations).

Invention 2: A compound described in Invention 1 wherein, ring A andring B when present respectively and independently represent a1,4-phenylene group, naphthalene-2,6-diyl group,1,2,3,4-tetrahydronaphthalene-2,6-diyl group, trans-1,4-cyclohexylenegroup or decahydronaphthalene-2,6-diyl group that may be substitutedwith fluorine atom(s).

Invention 3: A compound described in Invention 1 wherein, ring A or ringB when present respectively and independently represent a 1,4-phenylenegroup or trans-1,4-cyclohexylene group that may be substituted withfluorine atom(s).

Invention 4: A compound described in Invention 1 wherein, L and M whenpresent represent —CH₂CH₂—, —CH₂O—, —OCH₂—, —CF₂O—, —OCF₂—, —COO—,—OCO—, —CF═CF— or a single bond.

Invention 5: A compound described in Invention 1 wherein, L or Mrepresents a single bond.

Invention 6: A compound described in Invention 1 wherein, L and Mrepresent single bonds.

Invention 7: A compound described in Invention 1 wherein, 1≦m+n≦2.

Invention 8: A compound described in Invention 1 wherein, R representsan alkyl group, alkoxy group, alkenyl group or alkenyloxy group having1-12 carbon atoms.

Invention 9: A compound described in Invention 1 wherein Z represents ahalogen atom or an alkyl group, alkoxy group, alkenyl group, alkenyloxygroup or cyano group having 1-12 carbon atoms.

Invention 10: A compound described in Invention 1 wherein, R representsan alkyl group or alkenyl group having 1-12 carbon atoms, m represents1, n represents 1, ring A represents a trans-1,4-cyclohexylene group,ring B represents a 3-fluoro-1,4-phenylene group or3,5-difluoro-1,4-phenylene group, L and M represent single bonds, and Zrepresents a fluorine atom, chlorine atom, trifluoromethoxy group,difluoromethoxy group, trifluoromethyl group, 2,2,2-trifluoroethoxygroup or cyano group.

Invention 11: A compound described in Invention 1 wherein, R representsan alkyl group or alkenyl group having 1-12 carbon atoms, m represents0, n represents 1, ring B represents a 3-fluoro-1,4-phenylene group or3,5-difluoro-1,4-phenylene group, M represents a single bond and Zrepresents a fluorine atom, chlorine atom, trifluoromethoxy group,difluoromethoxy group, trifluoromethyl group, 2,2,2-trifluoroethoxygroup or cyano group.

Invention 12: A compound described in Invention 1 wherein, R and Zrepresent alkyl groups or alkenyl groups having 1-12 carbon atoms, m andn represent 1, rings A and B represent 1,4-phenylene groups ortrans-1,4-cyclohexylene groups, and L and M represent single bonds.

Invention 13: A compound described in Invention 1 wherein, R and Zrepresent alkyl groups or alkenyl groups having 1-12 carbon atoms, atleast one of R or Z represents an alkenyl group, m represents 1, nrepresents 0, rings A and B represent 1,4-phenylene groups ortrans-1,4-cyclohexylene groups, and L represents a single bond.

Invention 14: A compound represented by general formula (II):

(wherein, R⁴ represents an alkyl group, alkoxy group, alkenyl group,alkenyloxy group or alkoxyalkyl group, L¹ represents —CH₂CH₂—,—CH(CH₃)CH₂—, —CH₂CH(CH₃)—, —CH₂O—, —OCH₂—, —CF₂O—, —OCF₂—, —COO—,—OCO—, —CH═CH—, —CF═CF—, —C≡C—, —O(CH₂)₃—, —(CH₂)₃O—, —(CH₂)₄— or asingle bond, R⁴ represents an alkenyl group, alkenyloxy group oralkoxyalkyl group when L¹ represents a single bond, ring A and m are thesame as defined in general formula (I), and the decahydronaphthalenering has a trans form).

Invention 15: A production method of general formula (II) described inInvention 14 including: reducing a compound represented by generalformula (II-A):

(wherein, R⁴ is the same as previously defined in general formula (II),ring E represents a 1,4-phenylene group or trans-1,4-cyclohexylenegroup, L and m are the same as previously defined in general formula(I), and the decahydronaphthalene ring has a trans form), and oxidizingthe hydroxyl group as necessary.

Invention 16: A compound represented by general formula (V-1) or generalformula (V-2):

(wherein, U¹ and U² respectively and independently represent an oxygenatom or the following structure:

(wherein, k represents an integer from 1 to 7), L is the same aspreviously defined in general formula (I), and the decahydronaphthalenering has a trans form).

Invention 17: A production method of general formula (V-1) or generalformula (V-2) described in Invention 16 including: converting a compoundrepresented by general formula (V-1A) or general formula (V-2A):

(wherein, k is the same as previously defined in general formula (V-1)or general formula (V-2), and L is the same as previously defined ingeneral formula (I)) into an enamine using a secondary amine, andreacting it with methyl vinyl ketone to obtain a compound represented bygeneral formula (V-1B) or general formula (V-2B)

(wherein, k is the same as previously defined in general formula (V-1)or general formula (V-2), and L is the same as previously defined ingeneral formula (I)) followed by reductive hydrogenation.

Invention 18: A production method of general formula (V-1) described inInvention 16 including: reducing a compound represented by formula(V-1C):

oxidizing the hydroxyl groups as necessary, and protecting the carbonylgroups as necessary.

Invention 19: A production method of general formula (V-2) described inInvention 16 including: reducing a compound represented by generalformula (V-2C):

(wherein, although ring G represents a cyclohexane ring or benzene ring,a single bond(s) of the cyclohexane ring may be replaced by doublebond(s), and although rings F and H respectively and independentlyrepresent the following structures:

wherein, U¹ is the same as previously defined in general formula (V-1)or general formula (V-2)), a single bond(s) of the cyclohexane ring maybe replaced by double bond(s)), oxidizing the hydroxyl group asnecessary, and further protecting the carbonyl group as necessary.

Invention 20: A production method of general formula (V-1a):

(wherein, k is the same as previously defined in general formula (V-1)or general formula (V-2)), which is one of the structures of generalformula (V-1) described in Invention 16, including monoacetalation of acompound represented by general formula (V-1D):

Invention 21: A liquid crystal composition containing a compounddescribed in any of Inventions 1 through 13.

Invention 22: A liquid crystal device having for its constituent featurethe liquid crystal composition described in Invention 21.

Invention 23: An active matrix drive, liquid crystal device that usesthe liquid crystal composition described in Invention 21.

Invention 24: A super twisted nematic liquid crystal device that usesthe liquid crystal composition described in Invention 21.

BEST MODE FOR CARRYING OUT THE INVENTION

The following provides a detailed explanation of the present invention.A compound of general formula (I) provided in the present invention ispreferably of the form described below.

In general formula (I), although R and Z represent alkyl groups oralkoxy groups having 1-16 carbon atoms, alkenyl groups having 2-16carbon atoms, alkenyloxy groups having 3-16 carbon atoms, alkyl groupshaving 1-12 carbon atoms substituted with alkoxy group(s) having 1-10carbon atoms, hydrogen atoms, fluorine atoms, chlorine atoms,trifluoromethoxy groups, difluoromethoxy groups, trifluoromethyl groups,2,2,2-trifluoroethoxy groups, cyano groups, cyanato groups, hydroxylgroups or carboxyl groups, which may be substituted with halogen(s), astraight chain alkyl group having 1-12 carbon atoms or a straight chainalkenyl group having 2-12 carbon atoms is preferable, a straight chainalkyl group having 1-7 carbon atoms or a straight chain alkenyl grouphaving 2-7 carbon atoms is more preferable, and the following structuresare particularly preferable for R in the case of a straight chainalkenyl group:

(wherein, the right side is linked to a ring); a structure similar tothat in R is preferable for Z in the case the dielectric anisotropy ofthe compound is near 0 or negative, and a fluorine atom, chlorine atom,trifluoromethoxy group, difluoromethoxy group, trifluoromethyl group,2,2,2-trifluoroethoxy group or cyano group is preferable, a fluorineatom, trifluoromethoxy group or cyano group is more preferable, and afluorine atom or cyano group is particularly preferable for Z in thecase the dielectric anisotropy of the compound is positive. Although mand n respectively and independently represent an integer from 0 to 2and satisfy m+n≦3, they are preferably respectively and independently 0or 1, and more preferably satisfy 1≦m+n≦2. Ring A and ring B whenpresent may be the same or different, represent atrans-1,4-cyclohexylene group wherein one CH₂ group or more than oneadjacent CH₂ groups in the group may be replaced by —O— or —S—, or a1,4-phenylene group, 1,4-cyclohexenylene group,1,4-bicylo(2,2,2)octylene group, piperidine-1,4-diyl group,naphthalene-2,6-diyl group, trans-decahydronaphthalene-trans-2,6-diylgroup or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group wherein one CHgroup or more than one adjacent CH groups in the group may be replacedby —N═, and although these may be substituted with a cyano group orhalogen, a 1,4-phenylene group or trans-1,4-cyclohexylene group that maybe substituted with halogen is preferable, a trans-1,4-cyclohexylenegroup is more preferable for ring A, and a 1,4-phenylene group,3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group ortrans-1,4-cyclohexylene group is more preferable for ring B. Although Land M when present may be the same or different, and represent —CH₂CH₂—,—CH(CH₃)CH₂—, —CH₂CH(CH₃)—, —CH₂O—, —OCH₂—, —CF₂O—, —OCF₂—, —COO—,—OCO—, —CH═CH—, —CF═CF—, —C C—, —O(CH₂)₃—, —(CH₂)₃O—, —(CH₂)₄— or asingle bond, —CH₂CH₂— or a single bond is preferable for L while asingle bond is particularly preferable, and —COO—, —OCO—, —CH₂CH₂—, —CC— or a single bond is preferable for M, while a single bond isparticularly preferable.

(wherein, although R is the same as previously defined in formula (I), astraight chain alkyl group having 1-7 carbon atoms or a straight chainalkenyl group of the structure shown below is preferable, and althoughR¹ represents an alkenyl group having 2-16 carbon atoms, the followingstructure is preferable):

(wherein, the right side is linked to a ring).

The following forms are particularly preferable for the compound ofgeneral formula (V-1) or general formula (V-2) provided in the presentinvention:

(wherein, R¹ is the same as previously defined, and thedecahydronaphthalene ring represents the trans form); and,

(wherein, although R is the same as previously defined in formula (I), astraight chain alkyl group having 1-7 carbon atoms or a straight chainalkenyl group having the following structure is preferable, R is thesame as previously defined, and the decahydronaphthalene ring representsthe trans form).

A compound of general formula (I) can be produced based on the stepsindicated below. In addition, the production method of the compound ofgeneral formula (I) is not limited to the production examples describedbelow.

1. Synthesis of General Formula (I)—1

1-1 Synthesis of General Formula (Iaf) from General Formula (Iaa) andGeneral Formula (Ibf) from General Formula (Iba) in which R is an AlkylGroup, Alkoxy Group or Alkoxyalkyl Group

After reacting a decahydronaphthalene derivative represented by generalformula (IIa):

(wherein, R² represents an alkyl group, alkoxy group or alkoxyalkylgroup, ring A, m and L are the same as previously defined in generalformula (I), and the decahydronaphthalene ring has a trans form) withorganometallic reagent (III):

wherein, Z¹ represents an alkyl group, alkoxy group, alkyl groupsubstituted with an alkoxy group, hydrogen atom, fluorine atom, chlorineatom, trifluoromethoxy group, difluoromethoxy group, trifluoromethylgroup or 2,2,2-trifluoroethoxy group, Z², Z³ and Z⁴ respectively andindependently represent a hydrogen atom, fluorine atom or chlorine atom,W represents MgX (wherein, X represents a chlorine atom, bromine atom oriodine atom), a metal atom such as Li, B(OH)₂ or SiF(CH₃)₂, and thesecan be easily prepared from the corresponding halogenated benzenederivative), by dehydrating in the presence of acid catalyst,octahydronaphthalene derivative (IV):

(wherein, R², L, Z¹, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, and the 9,10 positions of the octahydronaphthalene ring havetrans forms) is obtained. By hydrogenating the double bond of theoctahydronaphthalene ring and isomerizing in the presence of alkalinecatalyst as necessary, (IA-1), which includes general formula (Iaf) fromgeneral formula (Iaa) and general formula (Ibf) from general formula(Iba):

(wherein, R², L, Z¹, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, and decahydronaphthalene ring has a trans form) can beproduced.1-2 Synthesis of General Formula (Iaf) from General Formula (Iaa) andGeneral Formula (Ibf) from General Formula (Iba) in which R is anAlkenyl Group

After reacting a decahydronaphthalene derivative represented by formula(V-1b) or general formula (V-2b):

(wherein, L is the same as previously defined in general formula (I),and the decahydronaphthalene ring has a trans form) with organometallicreagent (III), by dehydrating in the presence of acid catalyst andre-converting to acetal, general formula (VIa) or general formula (Vib):

(wherein, L, Z¹, Z², Z³ and Z⁴ are the same as previously defined, andthe 9,10 positions of the octahydronaphthalene ring have trans forms) isobtained. After hydrogenating the double bond of theoctahydronaphthalene ring and isomerizing in the presence of alkalinecatalyst as necessary followed by deacetalization, general formula(VIIa) or general formula (VIIb):

(wherein, L, Z¹, Z², Z³ and Z⁴ are the same as previously defined, andthe 9,10 positions of the octahydronaphthalene ring have trans forms) isobtained. After then reacting this with Wittig's reagent (VIII),Ph₃P═CHOCH₃  (VIII)it was acid hydrolyzed and isomerized to the trans form using basefollowed by repeating reaction of (VIII) and acid hydrolysis to obtainalkanal derivative (IX):

(wherein l represents an integer of 0 or greater, m, L, Z¹, Z², Z³ andZ⁴ are the same as previously defined, and the decahydronaphthalene ringhas a trans form). After reacting this with general formula (X):Ph₃P═CHR³  (X)(wherein, R³ represents a hydrogen atom or alkyl group that may besubstituted with one or more fluorine atoms or alkoxy groups), byisomerizing the double bond to the trans conformation using a benzenesulfinate and so forth as necessary, decahydronaphthalene derivative(IA-2), in which R of general formula (Iaf) from general formula (Iaa)and general formula (Ibf) from general formula (Iba) represents analkenyl group:

(wherein, l represents an integer of 0 or greater, R³, m, L, Z¹, Z², Z³and Z⁴ are the same as previously defined, and the decahydronaphthalenering has a trans form), can be produced. In addition, by reducingalkanal derivative (IX) to obtain an alcohol derivative and thenconverting this to an alkoxide followed by reacting the alkyl halide, acompound can be produced wherein, in general formula (I), n is 1, ring Cis a 1,4-phenylene group, and R is an alkoxy group, etc.1-3 Synthesis of General Formula (Iao) from General Formula (Iaj) andGeneral Formula (Ibo) from General Formula (Ibj)

After reacting Wittig's reagent (VIII) with general formula (IIa), byacid hydrolyzing, isomerizing to the trans form using base, againreacting with (VIII) and repeating acid hydrolysis, and reacting generalformula (III) with alkanal derivative (XI):

(wherein, R², L, ring A and m are the same as previously defined, andthe decahydronaphthalene ring has a trans form), followed by dehydratingin the presence of acid catalyst, decahydronaphthalene derivative (XII):

(wherein, R², L, Z¹, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, and the decahydronaphthalene ring has a trans form) isobtained. By hydrogenating the double bond, (IA-3), which includesgeneral formula (Iao) from general formula (Iaj) and general formula(Ibo) from general formula (Ibj):

(wherein, R², L, Z¹, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, and the decahydronaphthalene ring has a trans form) can beproduced.1-4 Synthesis of General Formula (Iai) from General Formula (Iag),General Formula (Iar) from General Formula (Iap), General Formula (Ibi)from General Formula (Ibg) and General Formula (Ibr) from GeneralFormula (Ibp)

After either direct bromination or iodination or lithionation with alkyllithium of a phenyldecahydro-naphthalene derivative represented bygeneral formula (XIII) for which the synthesis method has already beendescribed:

(wherein, R, L, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, M¹ represents a single bond or an alkylene group having 1-4carbon atoms, and the decahydronaphthalene ring has a trans form), byreacting with bromine or iodine, decahydronaphthalene derivative (XIV):

(wherein, Z⁵ represents a halogen atom such as bromine or iodine, R, L,Z², Z³, Z⁴, ring A and m are the same as previously defined, M¹represents a single bond or alkylene group having 1-4 carbon atoms, andthe decahydronaphthalene ring has a trans form) can be produced.

Organometallic reagent (XV):

(wherein, W¹ represents a metal such as MgBr, MgI or Li or ametal-containing group, R, L, Z², Z³, Z⁴, ring A and m are the same aspreviously defined, M¹ represents a single bond or an alkylene grouphaving 1-4 carbon atoms, and the decahydronaphthalene ring has a transform) is produced by reacting a metal such as magnesium with generalformula (XIV) or by converting general formula (XIII) to the trans-metalusing an organometallic reagent such as alkyl lithium. By reacting thiswith carbon dioxide, a benzoic acid derivative represented by generalformula (XVI):

(wherein, R, L, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, M¹ represents a single bond or an alkylene group having 1-4carbon atoms, and the decahydronaphthalene ring has a trans form) isobtained. After converting this to an acid halide with a halogenatingagent such as thionyl halide, by reacting with ammonia to convert anacid amide and then dehydrating, general formula (IA-4), which includesgeneral formula (Iai) from general formula (Iag), general formula (lar)from general formula (Iap), general formula (Ibi) from general formula(Ibg) and general formula (Ibr) from general formula (Ibp):

(wherein, R, L, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, M¹ represents a single bond or an alkenyl group having 1-4carbon atoms, and the decahydronaphthalene ring has a trans form) can beproduced.1-5 Production of General Formula (Iau) from General Formula (Ias) andGeneral Formula (Ibu) from General Formula (Ibs)

After acid chloridation of general formula (XVIII):

(wherein, R⁴ represents an alkyl group, alkenyl group, alkoxy group oralkoxyalkyl group, L, ring A and m are the same as previously defined,and the decahydronaphthalene ring has a trans form), obtained byreacting an oxidant such as silver oxide with general formula (XVII)obtained in the production process of general formula (XI) for which theproduction method has been already described:

(wherein, R⁴ represents an alkyl group, alkenyl group, alkoxy group oralkoxyalkyl group, L, ring A and m are the same as previously defined,and the decahydronaphthalene ring has a trans form), by reacting with acompound of general formula (XIX):

(wherein, Z is the same as previously described in general formula (I),and Z², Z³ and Z⁴ are the same as previously defined), general formula(IA-5), which includes general formula (Iau) from general formula (Ias)and general formula (Ibu) from general formula (Ibs):

(wherein, R⁴, L, Z² Z³, Z⁴, ring A and m are the same as previouslydefined, Z is the same as previously described in general formula (I),and the decahydronaphthalene ring has a trans form), can be produced.1-6 Production from General Formula (Ici) from General Formula (Ica) andGeneral Formula (Icu) from General Formula (Icm)

General formula (IA-6), which includes general formula (Ici) fromgeneral formula (Ida) and general formula (Icu) from general formula(Icm):

(wherein, R⁴, L, Z¹, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, Z², Z³ and Z⁴ may be the same or different, and thedecahydronaphthalene ring has a trans form), can be produced by reactinggeneral formula (III) with general formula (XIV), for which theproduction method has already been described, in the presence oftransition metal catalyst.1-7 Synthesis of General Formula (Idi) from General Formula (Ida)

General formula (IA-7), which includes general formula (Idi) fromgeneral formula (Ida):

(wherein, R⁴, L, Z¹, Z³ Z⁴ ring A and m are the same as previouslydefined, Z², Z³ and Z⁴ may be the same or different, and thedecahydronaphthalene ring has a trans form), can be produced using themethod described in 1-4 and a phenyldecahydronaphthalene derivativerepresented by general formula (IA-6a) for which the synthesis methodhas already been described:

(wherein, R⁴, L, Z¹, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, Z², Z³ and Z⁴ may be the same or different, and thedecahydronaphthalene ring has a trans form).1-8 Production of General Formula (Idu) from General Formula (Idm)

By converting general formula (XVIII), for which the production methodhas already been described, into an acid chloride followed by reactingwith a compound of general formula (XX):

(wherein, Z, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, and the plurality of Z², Z³ and Z⁴ may be the same ordifferent), general formula (IA-8), which includes general formula (Idu)from general formula (Idm):

(wherein, R⁴, L, Z, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, the plurality of Z², Z³ and Z⁴ may be the same or different,and the decahydronaphthalene ring has a trans form) can be produced.1-9 Production of General Formula (Ier) from General Formula (Iea)

General formula (IA-9), which includes general formula (Icr) fromgeneral formula (Ica):

(wherein, R⁴, L, Z¹, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, the plurality of Z², Z³ and Z⁴ may be the same or different,and the decahydronaphthalene ring has a trans form), can be produced byreacting general formula (XXI):

(wherein, Z¹, Z², Z³ and Z⁴ are the same as previously defined) withgeneral formula (XIV), for which the production method has already beendescribed, in the presence of transition metal catalyst.1-10 Production of General Formula (Iff) from General Formula (Ifa),General Formula (Ifo) from General Formula (Ifj) and General Formula(Iry) from General Formula (Irm)

After reacting an organometallic reagent (XXII)

(wherein, X¹, X², X³, X⁴ and X⁵ respectively and independently representa hydrogen atom, fluorine atom or chlorine atom, and W and Z¹ are thesame as previously defined) with a decahydronaphthalene derivativerepresented by general formula (IIa), by then dehydrating in thepresence of acid catalyst, hydrogenating the double bond of theoctahydronaphthalene ring, and isomerizing in the presence of alkalinecatalyst as necessary, (IA-10), which includes general formula (Iff)from general formula (Ifa), general formula (Ifo) from general formula(Ifj) and general formula (Iry) from general formula

(wherein, R², L, X¹, X², X³, X⁴, X⁵, Z¹, ring A and m are the same aspreviously defined, and the decahydronaphthalene ring has a trans form),can be produced.1-11 Synthesis of General Formula (Ifi) from General Formula (Ifg) andGeneral Formula (Ifr) from General Formula (Ifp)

After demethoxyating general formula (XXIII), for which the synthesismethod has already been described:

(wherein, R², L, X¹, X², X³, X⁴, X⁵, ring A and m are the same aspreviously defined, and the decahydronaphthalene ring has a trans form)using hydrobromic acid and so forth to obtain phenol derivative (XXIV):

(wherein, R², L, X¹, X², X³, X⁴, X⁵, ring A and m are the same aspreviously defined, and the decahydronaphthalene ring has a trans form),and converting to an elimination group by allowing p-toluene sulfonylchloride or trifluoromethane sulfonic acid anhydride to act on this, byreacting with potassium cyanate and so forth in the presence oftransition metal catalyst, general formula (IA-11), which includesgeneral formula (Ifi) from general formula (Ifg) and general formula(Ifr) from general formula (Ifp):

(wherein, R², L, X¹, X², X³, X⁴, X⁵, ring A and m are the same aspreviously defined, and the decahydronaphthalene ring has a trans form),can be produced. Here, a palladium complex or nickel complex ispreferable for the transition metal catalyst.1-12 Synthesis of General Formula (Igp) from General Formula (Iga)

After reducing decahydronaphthalene derivative (II) to obtain alcoholderivative (XXV):

(wherein, R², L, ring A and m are the same as previously defined, andthe decahydronaphthalene ring has a trans form), by either reacting thiswith a halogenating agent, p-toluene sulfonyl chloride ortrifluoromethane sulfonic acid anhydride, a compound represented bygeneral formula (XXVI):

(wherein, V represents a bromine or iodine halogen atom or anelimination group such as a p-toluene sulfonyloxy group or atrifluoromethane sulfonyloxy group, R², L, ring A and m are the same aspreviously defined, and the decahydronaphthalene ring has a trans form)is obtained. By then reacting this compound with a metal such asmagnesium or alkyl lithium and so forth, organometallic reagent (XXVII):

(wherein, W, R², L, ring A and m are the same as previously defined, andthe decahydronaphthalene ring has a trans form) is prepared, and afterreacting this with 1,2,3,4-tetrahydronaphthalene-2-one derivative(XXVIII):

(wherein, X¹, X², X³ and Z¹ are the same as previously defined), bydehydrating in the presence of acid catalyst to obtain1,2-dihydronaphthalene derivative followed by hydrogenating the doublebond of the 1,2-dihydronaphthalene ring, general formula (IA-12), whichincludes general formula (Igp) from general formula (Iga):

(wherein, R², L, X¹, X², X³, Z¹ ₁ ring A and m are the same aspreviously defined, and the decahydronaphthalene ring has a trans form),can be produced.1-13 Synthesis of General Formula (Igt) from General Formula (Igq)

General formula (IA-13), which includes general formula (Igt) fromgeneral formula (Igq):

(wherein, R², L, X¹, X², X³, ring A and m are the same as previouslydefined, and the decahydronaphthalene ring has a trans form), can beproduced by using the method described in 1-4 and aphenyldecahydronaphthalene derivative represented by general formula(IA-12a), for which the synthesis method has already been described:

(wherein, R², L, X¹, X², X³, ring A and m are the same as previouslydefined, and the decahydronaphthalene ring has a trans form).1-14 Synthesis of General Formula (Icl) from General Formula (Icj) andGeneral Formula (Icx) from General Formula (Icv)

After reacting organometallic reagent (XXVII) with formula (XXIX):

by preparing general formula (XXX):

(wherein, R², L, ring A and m are the same as previously defined, andthe octahydronaphthalene ring has a trans form) by dehydrating in thepresence of acid catalyst, hydrogenating the double bond and removingthe protection of the carbonyl groups under acidic conditions, generalformula (XXXI):

(wherein, R², L, ring A and m are the same as previously defined, andthe octahydronaphthalene ring has a trans form) is obtained. Afterreacting this with organometallic reagent (III), by dehydrating in thepresence of acid catalyst, hydrogenating the double bond of theoctahydronaphthalene ring and isomerizing in the presence of alkalinecatalyst as necessary, (IA-14), which includes general formula (Icl)from general formula (Icj) and general formula (Icx) from generalformula (Icv):

(wherein, R², L, Z¹, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, and the decahydronaphthalene ring has a trans form) can beproduced.1-15 Synthesis of General Formula (Idl) from General Formula (Idj)

General formula (IA-15), which includes general formula (Idl) fromgeneral formula (Idj):

(wherein, R², L, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, and the decahydronaphthalene ring has a trans form), can beproduced using the method described in 1-4 and aphenyldecahydronaphthalene derivative represented by general formula(IA-14a), for which the synthesis method has already been described:

(wherein, R², L, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, and the decahydronaphthalene ring has a trans form).1-16 Synthesis of General Formula (Idx) from General Formula (Idv)

With the exception of using for the raw material a phenol derivativethat can be produced from general formula (XXXI) or general formula(IA-1), for which the synthesis methods have already been described,general formula (IA-16), which includes general formula (Idx) fromgeneral formula (Idv):

(wherein, R², L, Z², Z³, Z⁴, Z, ring A and m are the same as previouslydefined, the plurality of A may be the same or different, and thedecahydronaphthalene ring has a trans form) can be produced using themethod described in 1-5.2. Synthesis of General Formula (I)—22-1 Synthesis of General Formula (Inj) from General Formula (Ina)

After reacting Wittig's reagent (VIII) with general formula (IIa), byhydrolyzing and isomerizing to the trans form using base and thenrepeating reaction with (VIII) and hydrolysis, alkanal derivative (L):

(wherein, l represents an integer of 0 or greater, R⁴, L, ring A and mare the same as previously defined, and the decahydronaphthalene ringhas a trans form) is obtained. After reacting this with general formula(X), by isomerizing the double bond to the trans conformation byallowing benzene sulfinic acid to act on the product as necessary,(IB-1), which includes general formula (Inj) from general formula (Ina):

(wherein, l represents an integer of 0 or greater, R⁴, R³, L, ring A andm are the same as previously defined, and the decahydronaphthalene ringhas a trans form), can be produced. In addition, after reducing alkanalderivative (XXIX) or general formula (IIa) to obtain an alcoholderivative and converting this to an alkoxide, by reacting with alkylhalide, a compound in which n=0 and Z is an alkoxy group and so forth ingeneral formula (I) can also be produced.2-2 Synthesis of General Formula (Ino) from General Formula (Ink)

(IB-2), which includes general formula (Inj) from general formula (Ina):

(wherein, R³, R⁴, L, ring A, l and m are the same as previously defined,and the decahydronaphthalene ring has a trans form), can be produced inthe same manner as 2-1 with the exception of using general formula(XXXI) as the raw material. In addition, after reducing the alkanalderivative or general formula (XXXI) to obtain an alcohol derivative andconverting this to an alkoxide in the same manner as 2-1, by reactingwith alkyl halide, a compound in which Z is an alkoxy group and so forthin general formula (I) can be produced. Furthermore, an alkenyl form ofgeneral formula (XXXI) can also be produced according to 1-2.2-3 Synthesis of General Formula (Iow) from General Formula (Ioa),General Formula (Ipe) from General Formula (Ipa), General Formula (Ipi)from General Formula (Ipg) and General Formula (Iqe) from GeneralFormula (Iqb) General formula (XXXII):

(wherein, ring A, R⁴, m, n, L, M¹, Z², Z³ and Z⁴ are the same aspreviously defined, ring D represents a 1,4-phenylene group ortrans-1,4-cyclohexylene group, and the decahydronaphthalene ring has atrans form), which can be produced by the above methods or theircombinations, can be obtained. An organometallic reagent is thenproduced that is prepared by directly iodinating or brominating this, orlithionating with alkyl lithium, and allowing the bromine or iodine toreact, followed by reacting with a metal such as magnesium ortransmetalating using an organometallic reagent such as alkyl lithium.By then allowing this to react with dimethylformamide (DMF), generalformula (XXXIII):

(wherein, ring A, ring D, R⁴, m, n, L, M¹, Z², Z³ and Z⁴ are the same aspreviously defined, and the decahydronaphthalene ring has a trans form)is produced. After allowing Wittig's reagent (VIII) to react with this,by hydrolyzing and isomerizing to the trans form using base, and thenrepeating reaction with (VIII) and hydrolysis, alkanal derivative(XXXIV):

(wherein, ring A, ring D, R⁴, l, m, n, L, M¹, Z², Z³ and Z⁴ are the sameas previously defined, and the decahydronaphthalene ring has a transform) is obtained. After reacting general formula (X) with this, byisomerizing the double bond to the trans conformation by allowingbenzene sulfinic acid to act on this as necessary, general formula(IB-3), which includes general formula (Iow) from general formula (Ioa),general formula (Ipe) from general formula (Ipa), general formula (Ipi)from general formula (Ipg) and general formula (Iqe) from generalformula (Iqb):

(wherein, ring A, ring D, R³, R⁴, l, m, n, L, M¹, Z², Z³ and Z⁴ are thesame as previously defined, and the decahydronaphthalene ring has atrans form), can be produced. In addition, after reducing alkanalderivative (XXXIV) to obtain an alcohol derivative and converting thisto an alkoxide, by reacting with alkyl halide, a compound can also beproduced in which R is an alkoxy group and so forth. Furthermore, theproduction method of a compound that does not contain an alkenyl grouphas been previously described.2-4 Synthesis of General Formula (Ira) from General Formula (Ipf)

General formula (IB-4), which includes general formula (Ipf) and generalformula (Ira):

(wherein, ring A, ring D, R³, R², m, n, 1, L and M¹ are the same aspreviously defined, and the decahydronaphthalene ring has a trans form),can be produced by the same method as 2-1 using general formula (XXXV):

(wherein, ring A, ring D, R², L, m, n and M¹ are the same as previouslydefined, and the decahydronaphthalene ring has a trans form), which canbe produced according to the method of 1-13 and 1-14.2-5 Synthesis of General Formula (Ipt) from General Formula (Ipk)

After reacting the following compound:

(wherein, R², Z², Z³, Z⁴ and W are the same as previously defined) withgeneral formula (VIIa) or general formula (VIIb), by dehydrating in thepresence of acid catalyst, hydrogenating the double bond of generalformula (XXXVIIa) or general formula (XXXVIIb):

(wherein, R², Z², Z³, Z⁴ and L are the same as previously defined, theplurality of R², Z², Z³ and Z⁴ may be the same or different, and thedecahydronaphthalene ring has a trans form) and isomerizing in thepresence of alkaline catalyst as necessary, general formula (IB-5),which includes general formula (Ipt) from general formula (Ipk):

(wherein, m, R², Z², Z³, Z⁴ and L are the same as previously defined,the plurality of R², Z², Z³ and Z⁴ may be the same or different, and thedecahydronaphthalene ring has a trans form), can be produced.2-6 Production of General Formula (Iqi) from General Formula (Iqf) andGeneral Formula (Iqt) from General Formula (Iqk)

General formula (IB-6), which includes general formula (Iqi) fromgeneral formula (Iqf) and general formula (Iqt) from general formula(Iqk):

(wherein, R⁴, L, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, the plurality of Z², Z³, Z⁴ and R⁴ may be the same ordifferent, and the decahydronaphthalene ring has a trans form), can beproduced by reacting general formula (XXXVI) with general formula (XIV),for which the production method has already been described, in thepresence of a transition metal catalyst.2-7 Synthesis of General Formula (Irf) from General Formula (Ira)

After reacting organometallic reagent (XXVII) with general formula (IIa)or general formula (XXVIII), by dehydrating in the presence of acidcatalyst and then hydrogenating the double bond, general formula (IB-7),which includes general formula (Igp) from general formula (Iga):

(wherein, R², L, Z², Z³, Z⁴, ring A and m are the same as previouslydefined, and the decahydronaphthalene ring has a trans form), can beproduced.2-8 Synthesis of General Formula (Irk) from General Formula (Irg)

After reacting the following compound:

(wherein, R², Z², Z³, Z⁴ and W are the same as previously defined) withgeneral formula (XXXI), by dehydrating in the presence of acid catalyst,hydrogenating the double bond of general formula (XXXIX):

(wherein, ring A, m, n, L, X⁴ and X⁵ are the same as previously defined,the plurality of R² may be the same or different, and thedecahydronaphthalene ring has a trans form), and isomerizing in thepresence of alkaline catalyst as necessary, general formula (IB-8),which includes general formula (Irk) from general formula (Irg):

(wherein, ring A, m, n, L, X⁴ and X⁵ are the same as previously defined,the plurality of R² may be the same or different, and thedecahydronaphthalene ring has a trans form), can be produced.3. Synthesis of General Formula (I)—33-1 By reacting a phenyl lithium reagent represented by general formula(XVa):

(wherein, R⁴, L, Z², Z³, Z⁴, ring A, M¹ and m are the same as previouslydefined, and the decahydronaphthalene ring has a trans form) with aphenyltrifluoroethylene derivative represented by general formula (XL):

(wherein, Z¹, Z², Z³ and Z⁴ are the same as previously defined) andde-protecting the protective groups as necessary, general formula(IC-1):

(wherein, R⁴, L, Z¹, Z², Z³, Z⁴, ring A, M¹ and m are the same aspreviously defined, the plurality of Z², Z³ and Z⁴ may be the same ordifferent, the steric form of the double bonds represents the transform, and the decahydronaphthalene ring has a trans form) can beproduced.3-2 By reacting a thiocarboxylate-O-ester represented by general formula(XLI):

(wherein, R², L, Z, Z², Z², Z⁴, ring A and m are the same as previouslydefined, the plurality of rings A may be the same or different, and thedecahydronaphthalene ring has a trans form) with a fluorinating agentsuch as DAST, and de-protecting the protective groups as necessary,general formula (IC-2):

(wherein, R², L, Z² Z³ Z⁴, Z, ring A and m are the same as previouslydefined, the plurality of rings A may be the same or different, and thedecahydronaphthalene ring has a trans form) can be produced.

Here, thiocarboxylate-O-ester can be produced by reacting thecorresponding carboxylate ester (IA-16) with Lawesson's reagent.3-3 General formula (IC-3):

(wherein, l is an integer of 0 or greater, R⁴, L, ring A and m are thesame as previously defined, and the decahydronaphthalene ring has atrans form) can be produced by reacting sodium chlorodifluoroacetatewith an alkanal derivative (L) to overheating.4. Synthesis of General Formula (I) Intermediates4-1 Synthesis of General Formula (II)

After reacting general formula (XLIII):

with general formula (XLIV):

(wherein, R⁴, W and m are the same as previously defined) in thepresence of a transition metal catalyst, by de-protecting the resultinggeneral formula (XLV):

(wherein, R⁴ and m are the same as previously defined), general formula(XLVI):

(wherein, R⁴ and m are the same as previously defined) is obtained. Bythen hydrogenating the aromatic rings of this compound, general formula(XLVII):

(wherein, R² and m are the same as previously defined) can be produced.In addition, after reacting general formula (XLVIII):

wherein, R⁴ is the same as previously defined, with general formula(XLIIIa):

(wherein, W is the same as previously defined) and dehydrating, generalformula (XLIX):

(wherein, R⁴ and m are the same as previously defined) is obtained.General formula (XLVII) can also be produced by hydrogenating thiscompound.4-2 Synthesis of General Formula (V-1)

Formula (V-1D) is obtained by hydrogenating formula (V-1C). Generalformula (V-1):

(wherein, U¹ and U² are the same as previously defined) can be producedby acetalation of the carbonyl groups followed by isolation of thediketone, monoacetal and diacetal.4-3 Synthesis of General Formula (V-2) General formula (LII):

(wherein, k is the same as previously defined) is obtained by reactinggeneral formula (XLIV) with general formula (V-1A), dehydrating,de-protecting the resulting compound and reacetalization. Generalformula (V-2) in which L is a single bond can then be produced byhydrogenating the aromatic ring of this compound and oxidizing oracetalating as necessary. In addition, general formula (LI):

(wherein, k is the same as previously defined) is obtained by reactinggeneral formula (XLIIIa) with general formula (V-1A), dehydrating,de-protecting the resulting compound and reacetalization. Generalformula (V-2) in which L is a single bond can then be produced byhydrogenating the aromatic rings of this compound and oxidizing oracetalating as necessary. Furthermore, in cases when L is not a singlebond, general formula (LIII) or general formula (LIV):

(wherein, k and L are the same as previously defined) is obtained inaccordance with the method described above. This compound can beobtained by hydrogenating using the method described above.

Specific examples of typical examples of compound (I) of the presentinvention produced in this manner are summarized in Table 1.

TABLE 1 Compound 1 Represented by General Formula (I): (I)

Phase transition Compound Formula temperature (° C.) I-1

C 52 (N 46) I I-2

oil I-3

C 46 I I-4

C 47 I I-5

— I-6

— I-7

— I-8

—

(In the table, C indicates the crystal phase, N the nematic phase, and Ian isotropic liquid.)

TABLE 2 Compound 2 Represented by General Formula (I): (I)

Phase transition Compound Formula temperature (° C.) I-9 

— I-10

C 86 (N 18) I I-11

C 80 N 129 I I-12

C 88 I I-13

— I-14

— I-15

—

(In the table, C indicates the crystal phase, N the nematic phase, and Ian isotropic liquid.)

TABLE 3 Compound 3 Represented by General Formula (I): (I)

Phase transition Compound Formula temperature (° C.) I-16

C 102 N 220 I I-17

C 62 N 188 I I-18

C 76 N 141 I I-19

C 94 N 215 I I-20

— I-21

C 96 N 107 I

(In the table, C indicates the crystal phase, N the nematic phase, and Ian isotropic liquid.)

TABLE 4 Compound 4 Represented by General Formula (I):

Phase transition Compound Formula temperature (° C.) I-22

oil I-23

C 24 N 115 I I-24

C 67 N 139 I I-25

C 30 N 99 I I-26

— I-27

— I-28

—

(In the table, C indicates the crystal phase, N the nematic phase, and Ian isotropic liquid.)

Since many of the compounds represented by general formula (I) exhibitsuperior co-solubility with other liquid crystal materials, they can besuitably used as materials for liquid crystal display cells in the stateof a mixture with other liquid crystal compounds. Although the compoundof (I) can be used in any of the various display methods previouslydescribed, they are suited for use in simple matrix driving or activematrix driving TN display elements and STN display elements.

In this manner, although compositions provided by the present inventioncontain at least one type of compound represented by general formula (I)as their first component for as preferable typical examples of nematicliquid crystal compounds that can be used by mixing with a compoundrepresented by general formula (I), they particularly preferably containat least one type of the second to fourth components indicated below asother components.

Namely, the second component is a so-called fluorine-based(halogen-based) p type liquid crystal compound that is composed of thecompounds indicated in general formulas (A1) through (A3) below.

In the above formulas, R^(b) represents an alkyl group having 1-12carbon atoms, these may have a straight chain or methyl or ethylbranched structure, a 3-6 membered ring structure, any arbitrary —CH₂—present in the group may be replaced by —O—, —CH═CH—, —CH═CF—, —CF═CH—,—CF═CF— or —C≡C—, and any arbitrary hydrogen atom present in the groupmay be substituted with a fluorine atom or trifluoromethoxy group.However, a straight chain alkyl group having 2-7 carbon atoms, straightchain 1-alkenyl group having 2-7 carbon atoms, straight chain 3-alkenylgroup having 4-7 carbon atoms and an alkyl group having 1-5 carbon atomsin which the terminal is substituted with an alkoxyl group having 1-3carbon atoms are preferable. In addition, the compound may have opticalactivity or be a racemic mixture in the case asymmetric carbons areformed as a result of branching.

Rings A, B and C respectively and independently represent atrans-1,4-cyclohexylene group, trans-decahydronaphthalene-trans-2,6-diylgroup, 1,4-phenylene group that may be substituted with one or morefluorine atoms, naphthalene-2,6-diyl group that may be substituted withone or more fluorine atoms, tetrahydronaphthalene-2,6-diyl group thatmay be substituted with one or more fluorine atoms, 1,4-cyclohexenylenegroup that may be substituted with a fluorine atom,1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group orpyridine-2,5-diyl group. However, a trans-1,4-cyclohexylene group,trans-decahydronaphthalene-trans-2,6-diyl group, naphthalene-2,6-diylgroup that may be substituted with a fluorine atom, or 1,4-phenylenegroup that may be substituted with 1 or 2 fluorine atoms is preferable.In particular, it is preferable that ring A be a trans-1,4-cyclohexylenegroup in the case ring B is a trans-1,4-cyclohexylene group ortrans-decahydronaphthalene-trans-2,6-diyl group, and it is preferablethat rings B and A be trans-1,4-cyclohexylene groups in the case ring Cis a trans-1,4-cyclohexylene group ortrans-decahydronaphthalene-trans-2,6-diyl group. In addition, it ispreferable that ring A be a trans-1,4-cyclohexylene group in (A3).

L^(a), L^(b) and L^(c) are connecting groups that respectively andindependently represent a single bond, ethylene group (—CH₂CH₂—),1,2-propylene group (—CH(CH₃)CH₂— and —CH₂CH(CH₃)—), 1,4-butylene group,—COO—, —OCO—, —OCF₂—, —CF₂O—, —CH═CH—, —CH═CF—, —CF═CH—, —CF═CF—, —C≡C—or —CH═NN═CH—. However, a single bond, ethylene group, 1,4-butylenegroup, —COO—, —OCF₂—, —CF₂O—, —CH═CF— or —C≡C— is preferable, and asingle bond or ethylene group is particularly preferable. In addition,it is preferable that at least one of these represent a single bond in(A2), and at least two of these represent a single bond in (A3).

Ring Z is an aromatic ring that can be represented by general formulas(La) through (Lc) below.

In these formulas, Y^(a) through Y^(j) respectively and independentlyrepresent a hydrogen atom or fluorine atom. However, it is preferablethat at least one of Y^(a) and Y^(b) be a fluorine atom in (La), and itis preferable that at least one of Y^(d) through Y^(f) be a fluorineatom in (Lb), with Y^(d) particularly preferably being a fluorine atom.

Terminal group P^(a) represents a fluorine atom, chlorine atom,trifluoromethoxy group, difluoromethoxy group, trifluoromethyl group ordifluoromethyl group, or an alkoxyl group, alkyl group, alkenyl group oralkenyloxy group having 2 or 3 carbon atoms and substituted by afluorine atom or more than one fluorine atoms. However, a fluorine atom,trifluoromethoxy group or difluoromethoxy group is preferable, and afluorine atoms is particularly preferable.

In addition, the compounds of general formula (I) of the presentinvention are excluded in (A2).

The third component is a so-called cyano-based p type liquid crystalcompound, and is composed of the compounds indicated with generalformulas (B1) through (B3) below.

In the above formulas, R^(c) represents an alkyl group having 1-12carbon atoms, and these may have a straight chain or methyl or ethylbranched structure, a 3-6 membered ring structure, any arbitrary —CH₂—present in the group may be replaced by —O—, —CH═CH—, —CH═CF—, —CF═CH—,—CF═CF— or —C≡C—, and any arbitrary hydrogen atom present in the groupmay be substituted with a fluorine atom or trifluoromethoxy group.However, a straight chain alkyl group having 2-7 carbon atoms, straightchain 1-alkenyl group having 2-7 carbon atoms, straight chain 3-alkenylgroup having 4-7 carbon atoms and an alkyl group having 1-5 carbon atomsin which the terminal is substituted with an alkoxyl group having 1-3carbon atoms are preferable. In addition, the compound may have opticalactivity or be a racemic mixture in the case asymmetric carbons areformed as a result of branching.

Rings D, E and F respectively and independently represent atrans-1,4-cyclohexylene group, trans-decahydronaphthalene-trans-2,6-diylgroup, 1,4-phenylene group that may be substituted with one or morefluorine atoms, naphthalene-2,6-diyl group that may be substituted withone or more fluorine atoms, tetrahydronaphthalene-2,6-diyl group thatmay be substituted with one or more fluorine atoms, 1,4-cyclohexenylenegroup that may be substituted with a fluorine atom,1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group orpyridine-2,5-diyl group. However, a trans-1,4-cyclohexylene group,trans-decahydronaphthalene-trans-2,6-diyl group, naphthalene-2,6-diylgroup that may be substituted with a fluorine atom, or 1,4-phenylenegroup that may be substituted with 1 or 2 fluorine atoms is preferable.In particular, it is preferable that ring D be a trans-1,4-cyclohexylenegroup in the case ring E is a trans-1,4-cyclohexylene group ortrans-decahydronaphthalene-trans-2,6-diyl group, and it is preferablethat rings D and E be trans-1,4-cyclohexylene groups in the case ring Fis a trans-1,4-cyclohexylene group ortrans-decahydronaphthalene-trans-2,6-diyl group. In addition, it ispreferable that ring D be a trans-1,4-cyclohexylene group in (B3).

L^(d), L^(e) and L^(f) are connecting groups that respectively andindependently represent a single bond, ethylene group (—CH₂CH₂—),1,2-propylene group (—CH(CH₃)CH₂— and —CH₂CH(CH₃)—), 1,4-butylene group,—COO—, —OCO—, —OCF₂—, —CF₂O—, —CH═CH—, —CH═CF—, —CF═CH—, —CF═CF—, —C≡C—,—OCH₂—, —CH₂O— or —CH═NN═CH—. However, a single bond, ethylene group,—COO—, —OCF₂—, —CF₂O—, —CF═CF— or —C≡C— is preferable, and a singlebond, ethylene group or —COO— is particularly preferable. In addition,it is preferable that at least one of these represent a single bond in(B2), and at least two of these represent a single bond in (B3).

Ring Y is an aromatic ring that can be represented by general formulas(Ld) through (Lf) below.

In these formulas, Y^(k) through Y^(q) respectively and independentlyrepresent a hydrogen atom or fluorine atom. However, Y^(n) and Y^(o) arepreferably hydrogen atoms in (Le). Although terminal group P^(b)represents a cyano group (—CN—), cyanato group (—OCN—) or —C═CCN, acyano group is preferable.

In addition, the compounds of general formula (I) of the presentinvention are excluded in (B2).

The fourth component is a non-polar liquid crystal having dielectricanisotropy of near 0, and is composed of the compounds indicated withgeneral formulas (C1) through (C3) below.

In the above formulas, R^(d) and P^(e) respectively and independentlyrepresent an alkyl group having 1-12 carbon atoms, and these may have astraight chain or methyl or ethyl branched structure, a 3-6 memberedring structure, any arbitrary —CH₂— present in the group may be replacedby —O—, —CH═CH—, —CH═CF—, —CF═CH—, —CF═CF— or —C≡C—, and any arbitraryhydrogen atom present in the group may be substituted with a fluorineatom or trifluoromethoxy group. However, a straight chain alkyl grouphaving 1-7 carbon atoms, straight chain 1-alkenyl group having 2-7carbon atoms, straight chain 3-alkenyl group having 4-7 carbon atoms andan alkyl group having 1-5 carbon atoms in which the terminal issubstituted with an alkoxyl group having 1-3 carbon atoms arepreferable. Moreover, it is more preferable that at least one of theserepresent a straight chain alkyl group having 1-7 carbon atoms, astraight chain 1-alkenyl group having 2-7 carbon atoms, or a straightchain 3-alkenyl group having 4-7 carbon atoms.

Rings G, H, I and J respectively and independently represent atrans-1,4-cyclohexylene group, trans-decahydronaphthalene-trans-2,6-diylgroup, 1,4-phenylene group that may be substituted with one or twofluorine atoms, naphthalene-2,6-diyl group that may be substituted withone or more fluorine atoms, tetrahydronaphthalene-2,6-diyl group thatmay be substituted with one or two fluorine atoms, 1,4-cyclohexenylenegroup that may be substituted with one or two fluorine atoms,1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group orpyridine-2,5-diyl group. However, it is preferable that in each compoundthere be no more than one trans-decahydronaphthalene-trans-2,6-diylgroup, naphthalene-2,6-diyl group that may be substituted with one ormore fluorine atoms, tetrahydronaphthalene-2,6-diyl group that may besubstituted with one or two fluorine atoms, 1,4-cyclohexenylene groupthat may be substituted with a fluorine atom, 1,3-dioxane-trans-2,5-diylgroup, pyrimidine-2,5-diyl group or pyridine-2,5-diyl group, and thatthe other rings be a trans-1,4-cyclohexylene group or a 1,4-phenylenegroup that may be substituted with 1 or 2 fluorine atoms or methylgroups.

L^(g), L^(h) and L^(i) are connecting groups that respectively andindependently represent a single bond, ethylene group (—CH₂CH₂—),1,2-propylene group (—CH(CH₃)CH₂— and —CH₂CH(CH₃)—), 1,4-butylene group,—COO—, —OCO—, —OCF₂—, —CF₂O—, —CH═CH—, —CH═CF—, —CF═CH—, —CF═CF—, —C≡C—or —CH═NN═CH—. However, a single bond, ethylene group, —COO—, —OCF₂—,—CF₂O—, —CF═CF— or —C≡C— is preferable, and a single bond, ethylenegroup, 1,4-butylene group, —COO—, —OCO—, —OCF₂—, —CF₂O—, —CF═CF—, —C—C—or —CH═NN═CH— is particularly preferable. In addition, it is preferablethat at least one of these represent a single bond in (C2), and at leasttwo of these represent a single bond in (C3).

In addition, the compounds of general formula (I) of the presentinvention are excluded in (C2).

More preferable forms in (C1) can be represented by general formulas(C1a) through (C1h) below.

In each of the above formulas, R^(f) and P^(g) respectively andindependently represent a straight chain alkyl group having 1-7 carbonatoms, straight chain 1-alkenyl group having 2-7 carbon atoms, straightchain 3-alkenyl group having 4-7 carbon atoms, straight chain alkoxylgroup having 1-3 carbon atoms or a straight chain alkyl group having 1-5carbon atoms in which the terminal is substituted with an alkoxyl grouphaving 1-3 carbon atoms. However, at least one of these represents astraight chain alkyl group having 1-7 carbon atoms, straight chain1-alkenyl group having 2-7 carbon atoms or straight chain 3-alkenylgroup having 4-7 carbon atoms. However, in the case rings G1 through G3are aromatic rings, the case of the corresponding R^(f) being a1-alkenyl group or alkoxyl group is excluded, and in the case rings H1through H3 are aromatic rings, the case of the corresponding R⁹ being a1-alkenyl group or alkoxyl group is excluded.

Rings G1 and H1 respectively and independently represent atrans-1,4-cyclohexylene group, trans-decahydronaphthalene-trans-2,6-diylgroup, 1,4-phenylene group that may be substituted with one or twofluorine atoms, naphthalene-2,6-diyl group that may be substituted withone or more fluorine atoms, tetrahydronaphthalene-2,6-diyl group thatmay be substituted with one or two fluorine atoms, 1,4-cyclohexenylenegroup that may be substituted with one or two fluorine atoms,1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group orpyridine-2,5-diyl group. However, it is preferable that in each compoundthere be no more than one trans-decahydronaphthalene-trans-2,6-diylgroup, naphthalene-2,6-diyl group that may be substituted with one ormore fluorine atoms, tetrahydronaphthalene-2,6-diyl group that may besubstituted with one or two fluorine atoms, 1,4-cyclohexenylene groupthat may be substituted with a fluorine atom, 1,3-dioxane-trans-2,5-diylgroup, pyrimidine-2,5-diyl group or pyridine-2,5-diyl group, and thatthe other rings in this case be a trans-1,4-cyclohexylene group or a1,4-phenylene group that may be substituted with 1 or 2 fluorine atomsor methyl groups. Rings G2 and H2 respectively and independentlyrepresent a trans-1,4-cyclohexylene group,trans-decahydronaphthalene-trans-2,6-diyl group, 1,4-phenylene groupthat may be substituted with one or two fluorine atoms or methyl groups,naphthalene-2,6-diyl group that may be substituted with one or morefluorine atoms, or tetrahydronaphthalene-2,6-diyl group that may besubstituted with one or two fluorine atoms. However, it is preferablethat in each compound there be no more than onetrans-decahydronaphthalene-trans-2,6-diyl group, naphthalene-2,6-diylgroup that may be substituted with one or more fluorine atoms ortetrahydronaphthalene-2,6-diyl group that may be substituted with one ortwo fluorine atoms, and that the other rings in this case be atrans-1,4-cyclohexylene group or a 1,4-phenylene group that may besubstituted with one or two fluorine atoms or methyl groups. Rings G3and H3 respectively and independently represent a 1,4-phenylene groupthat may be substituted with one or two fluorine atoms or methyl groups,naphthalene-2,6-diyl group that may be substituted with one or morefluorine atoms or tetrahydronaphthalene-2,6-diyl group that may besubstituted with one or two fluorine atoms. However, it is preferablethat in each compound there be no more than one naphthalene-2,6-diylgroup that may be substituted with one or more fluorine atoms ortetrahydronaphthalene-2,6-diyl group that may be substituted with one ortwo fluorine atoms.

More preferable forms in (C2) can be represented by general formulas(C2a) through (C2m) below.

In the above formulas, rings G1, G2, G3, H1, H2 and H3 are the same aspreviously defined, and ring I1 is the same as ring G1, ring I2 is thesame as ring G2 and ring I3 is the same as ring G3. In addition, it ispreferable that in each compound there be no more than onetrans-decahydronaphthalene-trans-2,6-diyl group, naphthalene-2,6-diylgroup that may be substituted with one or more fluorine atoms,tetrahydronaphthalene-2,6-diyl group that may be substituted with one ortwo fluorine atoms, 1,4-cyclohexenylene group that may be substitutedwith a fluorine atom, 1,3-dioxane-trans-2,5-diyl group,pyrimidine-2,5-diyl group or pyridine-2,5-diyl group, and that the otherrings in this case be a trans-1,4-cyclohexylene group or a 1,4-phenylenegroup that may be substituted with one or two fluorine atoms or methylgroups.

Next, more preferable forms in (C3) can be represented by generalformulas (C3a) through (C3f) below.

In the above formulas, rings G1, G2, H1, H2, I1 and I2 are the same aspreviously defined, and ring J1 is the same as ring G1 or ring J2 is thesame as ring G2. In addition, it is preferable that in each compoundthere be no more than one trans-decahydronaphthalene-trans-2,6-diylgroup, naphthalene-2,6-diyl group that may be substituted with one ormore fluorine atoms, tetrahydronaphthalene-2,6-diyl group that may besubstituted with one or two fluorine atoms, 1,4-cyclohexenylene groupthat may be substituted with a fluorine atom, 1,3-dioxane-trans-2,5-diylgroup, pyrimidine-2,5-diyl group or pyridine-2,5-diyl group, and thatthe other rings in this case be a trans-1,4-cyclohexylene group or a1,4-phenylene group that may be substituted with one or two fluorineatoms or methyl groups.

EXAMPLES

The present invention will be further described with reference toexamples of the present invention shown below. However, the presentinvention is not limited to these examples.

Example 1 Synthesis oftrans-6-propyl-trans-2-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene

3.6 g of magnesium was suspended in 3.5 ml of tetrahydrofuran (THF), anda 110 ml THF solution of 25.8 g of 1-bromo-3,4,5-trifluorobenzene wasadded dropwise to the suspension over a period of about 30 minutes atsuch a rate that the THF was moderately refluxed. After further stirringthe mixture for 1 hour, a 6 ml THF solution of 20 g of6-propyl-trans-decahydro-2-naphthalenone, which was obtained accordingto the above reference example, was added dropwise over a period of 30minutes. After further stirring the mixture for 2 hours, 50 ml of 10%hydrochloric acid was added. 100 ml of hexane was added, and the organicphase was separated. The aqueous phase was extracted with 100 ml ofhexane, and the extracts were combined with the organic phase. Thecombined organic phase was rinsed with water, a saturated aqueoussolution of sodium hydrogencarbonate, and a saturated saline solution,and dried on anhydrous sodium sulfate. The solvent was evaporated, and100 ml of toluene and 2.0 g of p-toluenesulfonic acid monohydrate wereadded. The mixture was heated at 110° C. with stirring while evaporatedwater was separated and removed. When the evaporation of water wasstopped, the temperature was reduced to room temperature. 50 ml of waterwas added, and the organic phase was separated. The organic phase wasrinsed with a saturated aqueous solution of sodium hydrogencarbonate,water and a saturated saline solution, and dried on anhydrous sodiumsulfate. The solvent was evaporated, and the whole amount of the residuewas dissolved in 200 ml of ethyl acetate. 2.5 g of palladium-carbon (5%,wet) was added, and the mixture was stirred in an autoclave in hydrogenunder a pressure of 400 KPa. After stirring for 5 hours at roomtemperature, the catalyst was removed by way of filtration throughcelite, and the solvent was evaporated to obtain a trans/cis mixture oftrans-6-propyl-2-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene. Thewhole amount of this mixture was dissolved in 55 ml ofN,N-dimethylformamide (DMF). 1 g of potassium t-butoxide was added tothe solution, and the mixture was stirred for 5 hours at 70° C. Afterthe mixture was cooled to room temperature, 100 ml of water was added,and extraction was performed twice using 100 ml of hexane. Organicphases were combined, and the combined organic phase was rinsed with adiluted hydrochloric acid, a saturated aqueous solution of sodiumhydrogencarbonate, water, and a saturated saline solution, and dried onanhydrous sodium sulfate. The solvent was evaporated, and the residuewas purified by silica gel column chromatography (hexane), andrecrystallized twice from ethanol to obtain 5 g white crystals oftrans-6-propyl-trans-2-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene.

IR(neat)1615, 1530 cm⁻¹

¹H NMR(Acetone-d₆)δ7.4-6.8(m,2H), 2.5-2.8(m,4H), 1.9-0.7(m,18H)

¹³C NMR(Acetone-d₆)δ154, 150, 140, 137, 146, 112, 43-34, 21, 15

MS m/z 310, 267, 247, 225, 211, 197, 185, 171, 158, 145, 135, 123, 109,95, 81, 67, 5 5

The following compounds were prepared in the same manner as mentionedabove:

-   trans-6-propyl-trans-2-(3,5-difluorophenyl)-trans-decahydronaphthalene,-   trans-6-propyl-trans-2-(4-fluorophenyl)-trans-decahydronaphthalene,-   trans-6-propyl-trans-2-(3,4-difluorophenyl)-trans-decahydronaphthalene,-   trans-6-propyl-trans-2-(4-trifluoromethoxyphenyl)-trans-decahydronaphthalene,-   trans-6-propyl-trans-2-(3-fluoro-4-trifluoromethoxyphenyl)-trans-decahydronaphthalene,-   trans-6-propyl-trans-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-decahydronaphthalene,-   trans-6-propyl-trans-2-(4-difluoromethoxyphenyl)-trans-decahydronaphthalene,-   trans-6-propyl-trans-2-(3-fluoro-4-difluoromethoxyphenyl)-trans-decahydronaphthalene,-   trans-6-propyl-trans-2-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-decahydronaphthalene,-   trans-6-propyl-trans-2-(4-chlorophenyl)-trans-decahydronaphthalene,-   trans-6-propyl-trans-2-(3-fluoro-4-chlorophenyl)-trans-decahydronaphthalene,-   trans-6-propyl-trans-2-(3,5-difluoro-4-chlorophenyl)-trans-decahydronaphthalene,-   trans-6-propyl-trans-2-(4-methoxyphenyl)-trans-decahydronaphthalene,-   trans-6-propyl-trans-2-(3-fluoro-4-methoxyphenyl)-trans-decahydronaphthalene,-   trans-6-propyl-trans-2-(3,5-difluoro-4-methoxyphenyl)-trans-decahydronaphthalene.

Example 2 Synthesis of6-(trans-4-propylcyclohexyl)-decahydro-2-naphthalenone

(2-a) Synthesis of6-(trans-4-propylcyclohexyl)-4,4a,5,6,7,8-hexahydro-3H-2-naphthalenone

200 g of 4-(trans-4-propylcyclohexyl)cyclohexanone and 135.2 g ofpyrrolidine were dissolved in 800 ml of toluene. The solution was heatedand stirred for 6 hours while water which is evaporated by azeotropicdistillation was removed. Azeotropic distillation of the solution wascarried out with toluene so that excessive pyrrolidine was removed, and1-(4-(trans-4-propylcyclohexyl)-cyclohexen-1-yl)-pyrrolidine wasobtained. The product as it was was cooled to room temperature, and 800ml of toluene was added again. The mixture was cooled in a water bath,and 150 ml toluene solution of 89 ml of methyl vinyl ketone was addeddropwise over a period of 2 hours at 20° C. or less. After the dropwiseaddition was completed, the temperature was increased over a period of 2hours to reach the reflux temperature. The solution was cooled to roomtemperature, and a buffer solution of pH 5 which was prepared from B5.2g of sodium acetate, 104.2 ml of acetic acid, and 104.2 ml of water wasadded. Reflux was further continued for 5 hours. After the solution wascooled to room temperature, the organic phase was separated and rinsedwith water and a saturated saline solution. The organic phase was driedon anhydrous sodium sulfate. The solvent was evaporated, and 313 g of6-(trans-4-propylcyclohexyl)-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenonewas obtained.

(2-b) Synthesis of6-(trans-4-propylcyclohexyl)-octahydro-2-naphthalenone

21.8 g of metal lithium was added to 1500 ml of liquid ammonia which iscooled to −40° C. To the mixture, a 1200 ml THF solution of 313 g of6-(trans-4-propylcyclohexyl)-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenonewhich was obtained in (1-a) and 91 g of t-butanol were added dropwise at−35° C. Stirring was carried out for 30 minutes, and 50 g of ammoniumchloride was added to stop the reaction. The temperature was graduallyraised to evaporate ammonia. 200 ml of saturated aqueous solution ofammonium chloride and 400 ml of toluene were added. The organic phasewas separated and rinsed with water and a saturated saline solution. Theorganic phase was dried on anhydrous sodium sulfate. The solvent wasevaporated, and distillation was carried out (bp.=180° C., 0.03 Ps) toobtain 96 g of 6-(trans-4-propylcyclohexyl)-octahydro-2-naphthalenone.

IR(nujol) 1718 cm−1

¹H NMR(CDCl₃)□2.4-2.2(m,4H), 1.8-1.6(m,5H), 1.4-1.0(m,20H), 0.9(t,3H)

¹³C NMR(CDCl₃)□212, 48, 44, 42, 40, 38, 37, 35, 34, 30, 29, 20, 14.

MS m/z 276, 258, 232, 152, 135, 125, 110, 95, 83, 69, 55

The following compounds were prepared in the same manner as mentionedabove:

-   6-(trans-4-methylcyclohexyl)-octahydro-2-naphthalenone,-   6-(trans-4-ethylcyclohexyl)-octahydro-2-naphthalenone,-   6-(trans-4-butylcyclohexyl)-octahydro-2-naphthalenone,-   6-(trans-4-pentylcyclohexyl)-octahydro-2-naphthalenone,-   6-(trans-4-hexylcyclohexyl)-octahydro-2-naphthalenone,-   6-(trans-4-heptylcyclohexyl)-octahydro-2-naphthalenone.

Example 3 Synthesis oftrans-6-(trans-4-propylcyclohexyl)-2-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene

2.1 g of magnesium was suspended in 4 ml of THF, and a 65 ml THFsolution of 16.8 g of 1-bromo-3,4,5-trifluorobenzene was added dropwiseto the suspension over a period of about 30 minutes at such a rate thatthe THF was moderately refluxed. After further stirring the mixture for1 hour, an 80 ml THF solution of 20 g of6-(trans-4-propylcyclohexyl)-octahydro-2-naphthalenone, which wasobtained Example 1, was added dropwise for 30 minutes. After furtherstirring the mixture for 2 hours, 50 ml of 10% hydrochloric acid wasadded. 100 ml of hexane was added, and the organic phase was separated.The aqueous phase was extracted with 100 ml of hexane, and the extractswere combined with the organic phase. The combined organic phase wasrinsed with water, a saturated aqueous solution of sodiumhydrogencarbonate, and a saturated saline solution, and dried onanhydrous sodium sulfate. The solvent was evaporated, and 100 ml oftoluene and 2.0 g of p-toluenesulfonic acid monohydrate were added. Themixture was heated at 110° C. with stirring while evaporated water wasseparated and removed. When the evaporation of water was stopped, thetemperature was reduced to room temperature. 50 ml of water was added,and the organic phase was separated. The organic phase was rinsed with asaturated aqueous solution of sodium hydrogencarbonate, water and asaturated saline solution, and dried on anhydrous sodium sulfate. Thesolvent was evaporated, and the whole amount of the residue wasdissolved in 200 ml of ethyl acetate. 2.5 g of palladium-carbon (5%,wet) was added, and the mixture was stirred in an autoclave in hydrogenunder a pressure of 400 KPa. After stirring for 5 hours at roomtemperature, the catalyst was removed by way of filtration throughcelite, and the solvent was evaporated to obtain a trans/cis mixture of6-(trans-4-propylcyclohexyl)-2-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene.The whole amount of this mixture was dissolved in 55 ml ofN,N-dimethylformamide (DMF). 0.7 g of potassium t-butoxide was added tothe solution, and the mixture was stirred for 2 hours at 50° C. Afterthe mixture was cooled to room temperature, 100 ml of water was added,and extraction was performed twice using 100 ml of hexane. Organicphases were combined, and the combined organic phase was rinsed with adiluted hydrochloric acid, a saturated aqueous solution of sodiumhydrogencarbonate, water, and a saturated saline solution, and dried onanhydrous sodium sulfate. The solvent was evaporated, and the residuewas purified by silica gel column chromatography (hexane), andrecrystallized twice from ethanol to obtain 7.2 g white crystals oftrans-6-(trans-4-propylcyclohexyl)-2-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene.

IR(nujol)1615, 1533 cm−1

¹H NMR(CDCl₃)□7.4-6.8(m,2H), 2.5-2.8(m,4H), 1.9-0.7(m,28H)

¹³C NMR(CDCl₃)□153, 149, 139, 136, 144, 110, 43-34, 20, 14

MS m/z 392, 267, 197, 185, 171, 158, 145, 125, 108, 95, 83, 69, 55

The following compounds were prepared in the same manner as mentionedabove:

-   trans-6-(trans-4-propylcyclohexyl)-trans-2-(3,5-difluorophenyl)-trans-decahydronaphthalene,-   trans-6-(trans-4-propylcyclohexyl)-trans-2-(4-fluorophenyl)-trans-decahydronaphthalene,-   trans-6-(trans-4-propylcyclohexyl)-trans-2-(3,4-difluorophenyl)-trans-decahydronaphthalene,-   trans-6-(trans-4-propylcyclohexyl)-trans-2-(4-trifluoromethoxyphenyl)-trans-decahydronaphthalene,-   trans-6-(trans-4-propylcyclohexyl)-trans-2-(3-fluoro-4-trifluoromethoxyphenyl)-trans-decahydronaphthalene,-   trans-6-(trans-4-propylcyclohexyl)-trans-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-decahydronaphthalene,-   trans-6-(trans-4-propylcyclohexyl)-trans-2-(4-difluoromethoxyphenyl)-trans-decahydronaphthalene,-   trans-6-(trans-4-propylcyclohexyl)-trans-2-(3-fluoro-4-difluoromethoxyphenyl)-trans-decahydronaphthalene,-   trans-6-(trans-4-propylcyclohexyl)-trans-2-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-decahydronaphthalene,-   trans-6-(trans-4-propylcyclohexyl)-trans-2-(4-chlorophenyl)-trans-decahydronaphthalene,-   trans-6-(trans-4-propylcyclohexyl)-trans-2-(3-fluoro-4-chlorophenyl)-trans-decahydronaphthalene,-   trans-6-(trans-4-propylcyclohexyl)-trans-2-(3,5-difluoro-4-chlorophenyl)-trans-decahydronaphthalene,-   trans-6-(trans-4-propylcyclohexyl)-trans-2-(4-methoxyphenyl)-trans-decahydronaphthalene,-   trans-6-(trans-4-propylcyclohexyl)-trans-2-(3-fluoro-4-methoxyphenyl)-trans-decahydronaphthalene,-   trans-6-(trans-4-propylcyclohexyl)-trans-2-(3,5-difluoro-4-methoxyphenyl)-trans-decahydronaphthalene.

Example 4 Synthesis oftrans-6-(3,5-difluorophenyl)-trans-decahydronaphthalene-2-carbaldehyde

13.5 g of methoxymethyltriphenylphosphonium chloride was suspended in 35ml of THF. While the suspension was cooled to 10° C. or lower, a 25 mlTHF solution of 5.5 g of potassium t-butoxide was added dropwise. Whilethe cooling was further continued, 25 ml THF solution of 8.5 g of6-(3,5-difluorophenyl)decahydronaphthalen-2-one was added dropwise overa period of 10 minutes. After the temperature was reduced to roomtemperature and stirring was carried out for 4 hours, water and hexanewere added. The organic phase was separated, and rinsed with water.Then, the solvent was evaporated. 10.1 g of the solid substance obtainedwas dissolved in 50 ml of THF. 50 ml of 10% hydrochloric acid was added,and the mixture was heated under refluxing for 2 hours. The temperaturewas reduced to room temperature. The organic phase was separated, andthe aqueous phase was extracted with ethyl acetate. The organic phaseswere combined, and the combined organic phase was rinsed with saturatedsaline solution. The solvent was then evaporated. 10 g of the oilysubstance obtained was dissolved in 100 ml of methanol. To the solution,which was cooled to 10° C. or lower, 10 ml of 10% aqueous solution ofsodium hydroxide was added. After stirring for 2 hours, the temperaturewas reduced to room temperature. Water was added to the mixture, and themixture was extracted with ethyl acetate. The organic phase was rinsedwith a saturated saline solution, and dried on anhydrous sodium sulfate.The solvent was evaporated, and 10.5 g oftrans-6-(3,5-difluorophenyl)-trans-decahydronaphthalene-2-carbaldehydeas an oily substance was obtained.

The following compounds were prepared in the same manner as mentionedabove:

-   trans-6-(4-fluorophenyl)-trans-decahydronaphthalene-2-carbaldehyde,-   trans-6-(3,4-difluorophenyl)-trans-decahydronaphthalene-2-carbaldehyde,-   trans-6-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene-2-carbaldehyde,-   trans-6-(4-trifluoromethoxyphenyl)-trans-decahydronaphthalene-2-carbaldehyde,-   trans-6-(3-fluoro-4-trifluoromethoxyphenyl)-trans-decahydronaphthalene-2-carbaldehyde,-   trans-6-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-decahydronaphthalene-2-carbaldehyde,-   trans-6-(4-difluoromethoxyphenyl)-trans-decahydronaphthalene-2-carbaldehyde,-   trans-6-(3-fluoro-4-difluoromethoxyphenyl)-trans-decahydronaphthalene-2-carbaldehyde,-   trans-6-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-decahydronaphthalene-2-carbaldehyde,-   trans-6-(4-chlorophenyl)-trans-decahydronaphthalene-2-carbaldehyde,-   trans-6-(3-fluoro-4-chlorophenyl)-trans-decahydronaphthalene-2-carbaldehyde,-   trans-6-(3,5-difluoro-4-chlorophenyl)-trans-decahydronaphthalene-2-carbaldehyde,-   trans-6-(4-methoxyphenyl)-trans-decahydronaphthalene-2-carbaldehyde,-   trans-6-(3-fluoro-4-methoxyphenyl)-trans-decahydronaphthalene-102-carbaldehyde,-   trans-6-(3,5-difluoro-4-methoxyphenyl)-trans-decahydronaphthalene-2-carbaldehyde.

Example 5trans-6-(3,4-difluorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene

13.5 g of methoxymethyltriphenylphosphonium chloride was suspended in 35ml of THF. While the suspension was cooled to 10° C. or lower, a 25 mlTHF solution of 5.5 g of potassium t-butoxide was added dropwise. Whilethe cooling was further continued, 25 ml THF solution of 10.0 g oftrans-6-(3,4-difluorophenyl)-trans-decahydronaphthalene-2-carbaldehyde,which was obtained in a manner similar to that of Example 1, was addeddropwise. After the temperature was reduced to room temperature andstirring was carried out for 4 hours, water and hexane were added. Theorganic phase was separated, and rinsed with water. Then, the solventwas evaporated. 12.0 g of the solid substance obtained was dissolved in60 ml of THF. 60 ml of 10% hydrochloric acid was further added, and themixture was heated under refluxing for 2 hours. The temperature wasreduced to room temperature. The organic phase was separated, and theaqueous phase was extracted with ethyl acetate. The organic phases werecombined, and the combined organic phase was rinsed with saturatedsaline solution. The solvent was then evaporated. 11.0 g oftrans-6-(3,4-difluorophenyl)-trans-decahydronaphthalene-2-carbaldehydeobtained was dissolved in 40 ml of THF. The solution was added againdropwise to a 60 ml THF solution of 13.5 g ofmethoxymethyltriphenylphosphonium chloride and 5.5 g of potassiumt-butoxide, which has been cooled. The temperature was reduced to roomtemperature. After the mixture was stirred for 4 hours, water and hexanewere added, and the organic phase was separated. After the organic phasewas rinsed with water, the solvent was evaporated. 13.6 g of the solidsubstance obtained was dissolved in 70 ml of THF. 70 ml of 10%hydrochloric acid was added to the solution, and the mixture was stirredfor 2 hours. The temperature was reduced to room temperature, water wasadded to the mixture, and the mixture was extracted with ethyl acetate.The organic phase was rinsed with a saturated saline solution, and driedon anhydrous sodium sulfate. The solvent was evaporated, and 12.0 g oftrans-6-(3,4-difluorophenyl)-trans-2-(2-formylethyl)decahydronaphthaleneas an oily substance was obtained.

The following compounds were prepared in the same manner as mentionedabove:

-   trans-6-(3,5-difluorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene,-   trans-6-(4-fluorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene,-   trans-6-(3,4,5-trifluorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene,-   trans-6-(4-trifluoromethoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-trifluoromethoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene,-   trans-6-(4-difluoromethoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-difluoromethoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene,-   trans-6-(4-chlorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-chlorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-chlorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene,-   trans-6-(4-methoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-methoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-methoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene.

Example 6 Synthesis oftrans-6-(3,5-difluorophenyl)-trans-2-vinyldecahydronaphthalene

24.4 g of methyltriphenylphosphonium iodide was suspended in 75 ml ofTHF. While the suspension was cooled to 10° C. or lower, a 40 ml THFsolution of 7.6 g of potassium t-butoxide was added dropwise. While thecooling was further continued, 100 ml THF solution of 20.5 g oftrans-6-(3,5-difluorophenyl)-trans-decahydronaphthalene-2-carbaldehyde,which was obtained in Example 1, was added dropwise. After thetemperature was reduced to room temperature and stirring was carried outfor 3 hours, water and hexane were added. The organic phase wasseparated, rinsed with water, and dried on anhydrous sodium sulfate.Then, the solvent was evaporated. 12.1 g of the oily substance obtainedwas purified by silica gel column chromatography (hexane), and 4.0 g oftrans-6-(3,5-difluorophenyl)-trans-2-vinyldecahydronaphthalene as anoily substance was obtained.

The following compounds were prepared in the same manner as mentionedabove:

-   trans-6-(4-fluorophenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3,4-difluorophenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3,4,5-trifluorophenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(4-trifluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3-fluoro-4-trifluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(4-difluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3-fluoro-4-difluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(4-chlorophenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3-fluoro-4-chlorophenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3,5-difluoro-4-chlorophenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(4-methoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3-fluoro-4-methoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3,5-difluoro-4-methoxyphenyl)-trans-2-vinyldecahydronaphthalene.

Example 7 Synthesis oftrans-6-(3,4,5-trifluorophenyl)-trans-2-(1-propenyl)decahydronaphthalene

13.4 g of ethyltriphenylphosphonium bromide was suspended in 30 ml ofTHF. While the suspension was cooled to 10° C. or lower, a 25 ml THFsolution of 4.5 g of potassium t-butoxide was added dropwise. While thecooling was further continued, 50 ml THF solution of 10.1 g oftrans-6-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene-2-carbaldehyde,which was obtained in a manner similar to that of Example 1, was addeddropwise. After the temperature was reduced to room temperature andstirring was carried out for 3 hours, water and hexane were added. Theorganic phase was separated, rinsed with water, and dried on anhydroussodium sulfate. Then, the solvent was evaporated. 9.1 g of the oilysubstance obtained was dissolved in 50 ml of toluene. 2.5 g of sodiumbenzenesulfinate and 10 ml of 10% hydrochloric acid were added to thesolution, and the mixture was heated under refluxing for 20 hours. Thetemperature was reduced to room temperature. The organic phase wasextracted using toluene, rinsed with a saturated aqueous solution ofsodium hydrogen carbonate and a saturated saline solution, in sequence,and dried on anhydrous sodium sulfate. Then, the solvent was evaporated.The resultant was purified by silica gel column chromatography (hexane),and recrystallized (in ethanol) to obtain 7.8 g of white solidtrans-6-(3,4,5-trifluorophenyl)-trans-2-(1-propenyl)decahydronaphthalene(I-6).

The following compounds were prepared in the same manner as mentionedabove:

-   trans-6-(3,5-difluorophenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(4-fluorophenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(3,4-difluorophenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(4-trifluoromethoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-trifluoromethoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(4-difluoromethoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-difluoromethoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(4-chlorophenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-chlorophenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-chlorophenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(4-methoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-methoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-methoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(3,4,5-trifluorophenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3,5-difluorophenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(4-fluorophenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3,4-difluorophenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(4-trifluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3-fluoro-4-trifluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(4-difluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3-fluoro-4-difluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(4-chlorophenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3-fluoro-4-chlorophenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3,5-difluoro-4-chlorophenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(4-methoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3-fluoro-4-methoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3,5-difluoro-4-methoxyphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3,4,5-trifluorophenyl)-trans-2-(1-pentenyl)decahydronaphthalene,-   trans-6-(3,5-difluorophenyl)-trans-2-(1-pentenyl)decahydronaphthalene,-   trans-6-(4-fluorophenyl)-trans-2-(1-pentenyl)decahydronaphthalene,-   trans-6-(3,4-difluorophenyl)-trans-2-(1-pentenyl)decahydronaphthalene,-   trans-6-(4-trifluoromethoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-trifluoromethoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene,-   trans-6-(4-difluoromethoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-difluoromethoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene,-   trans-6-(4-chlorophenyl)-trans-2-(1-pentenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-chlorophenyl)-trans-2-(1-pentenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-chlorophenyl)-trans-2-(1-pentenyl)decahydronaphthalene,-   trans-6-(4-methoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-methoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-methoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene.

Example 8 Synthesis oftrans-6-(3,4-difluorophenyl)-trans-2-(3-butenyl)decahydronaphthalene

16.5 g of methyltriphenylphosphonium iodide was suspended in a mixtureof 17 ml THF and 51 ml toluene. While the suspension was cooled to 10°C. or lower, a 4.6 g of potassium t-butoxide was added. While thecooling was further continued, 20 ml toluene solution of 5.0 g oftrans-6-(3,4-difluorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene,which was obtained in Example 2, was added dropwise. After the mixturewas stirred for 2 hours, 5 ml of water and then 200 ml of hexane wereadded, and triphenylphosphine oxide was separated by filtration. Theorganic phase was separated, rinsed with 100 ml of water and 100 ml ofwater/methanol mixed solvent (1/2), and dried on anhydrous sodiumsulfate. Then, the solvent was evaporated. The oily substance obtainedwas purified by silica gel column chromatography (hexane) andrecrystallized from ethanol to obtain 3.7 g of white solidtrans-6-(3,4-difluorophenyl)-trans-2-(3-butenyl)decahydronaphthalene(I-5).

The following compounds were prepared in the same manner as mentionedabove:

-   trans-6-(3,5-difluorophenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(4-fluorophenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(3,4,5-trifluorophenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(4-trifluoromethoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-trifluoromethoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(4-difluoromethoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-difluoromethoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(4-chlorophenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-chlorophenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-chlorophenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(4-methoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-methoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-methoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(3,4,5-trifluorophenyl)-trans-2-(3-pentenyl)decahydronaphthalene,-   trans-6-(3,5-difluorophenyl)-trans-2-(3-pentenyl)decahydronaphthalene,-   trans-6-(4-fluorophenyl)-trans-2-(3-pentenyl)decahydronaphthalene,-   trans-6-(3,4-difluorophenyl)-trans-2-(3-pentenyl)decahydronaphthalene,-   trans-6-(4-trifluoromethoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-trifluoromethoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene,-   trans-6-(4-difluoromethoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-difluoromethoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene,-   trans-6-(4-chlorophenyl)-trans-2-(3-pentenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-chlorophenyl)-trans-2-(3-pentenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-chlorophenyl)-trans-2-(3-pentenyl)decahydronaphthalene,-   trans-6-(4-methoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-methoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-methoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene.

Example 9 Synthesis oftrans-2-propyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene

(9-a) Synthesis oftrans-2-propyl-trans-6-(3,5-difluorophenyl)-trans-decahydronaphthalene

2.4 g of magnesium was suspended in 5 ml of tetrahydrofuran, and an 80ml THF solution of 17.6 g of 1-bromo-3,5-difluorobenzene was addeddropwise to the suspension over a period of about 30 minutes at such arate that the THF was moderately refluxed. After further stirring themixture for 1 hour, an 80 ml THF solution of 20 g of6-propyloctahydro-2-naphthalenone was added dropwise over a period of 30minutes. After further stirring the mixture for 2 hours, 80 ml of 10%hydrochloric acid was added. 100 ml of hexane was added, and the organicphase was separated. The aqueous phase was extracted with 100 ml ofhexane, and the extracts were combined with the organic phase. Thecombined organic phase was rinsed with water, a saturated aqueoussolution of sodium hydrogencarbonate, and a saturated saline solution,and dried on anhydrous sodium sulfate. The solvent was evaporated, and105 ml of toluene and 1.7 g of p-toluenesulfonic acid monohydrate wereadded. The mixture was heated at 110° C. with stirring while evaporatedwater was separated and removed. When the evaporation of water wasstopped, the temperature was reduced to room temperature. 50 ml of waterwas added, and the organic phase was separated. The organic phase wasrinsed with a saturated aqueous solution of sodium hydrogencarbonate,water and a saturated saline solution, and dried on anhydrous sodiumsulfate. The solvent was evaporated, and the whole amount of the residuewas dissolved in 100 ml of ethyl acetate. 3.0 g of carbon with 5%palladium was added, and the mixture was stirred in an autoclave inhydrogen under a pressure of 400 KPa. After stirring for 5 hours at roomtemperature, the catalyst was removed by way of filtration throughcelite, and the solvent was evaporated to obtain a trans/cis mixture oftrans-6-propyl-2-(3,5-difluorophenyl)-trans-decahydronaphthalene. Thewhole amount of this mixture was dissolved in 100 ml ofN,N-dimethylformamide (DMF). 2.4 g of potassium t-butoxide was added tothe solution, and the mixture was stirred for 5 hours at 70° C. Afterthe mixture was cooled to room temperature, 100 ml of water was added,and extraction was performed twice using 100 ml of toluene. Organicphases were combined, and the combined organic phase was rinsed with 10%hydrochloric acid, a saturated aqueous solution of sodiumhydrogencarbonate, water, and a saturated saline solution, and dried onanhydrous sodium sulfate. The solvent was evaporated, and the residuewas purified by silica gel column chromatography (hexane), andrecrystallized from ethanol to obtain 16.5 g white crystals oftrans-6-propyl-trans-2-(3,5-difluorophenyl)-trans-decahydronaphthalene.

(9-b) Synthesis oftrans-2-propyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene

16.5 oftrans-6-propyl-trans-2-(3,5-difluorophenyl)-trans-decahydronaphthalene,which was obtained in (9-a), was dissolved in 70 ml of THF, and thesolution was cooled to −78° C. 38.6 ml of 1.6 M butyl lithium-hexanesolution was added over a period of 30 minutes in a manner such that theinner temperature does not exceed −50° C. After further stirring for 20minutes, maintaining the inner temperature under −50° C., carbon dioxidewas injected into the mixture. When generation of heat stopped, thetemperature was gradually increased to room temperature. 50 ml of waterand 50 ml of hexane was added, and the organic phase was separated. Theorganic phase was rinsed with water and a saturated saline solution, anddried on anhydrous sodium sulfate. The solvent was evaporated, and thewhole amount of the residue was dissolved in 170 ml of1,2-dichloroethane. 8.1 μg of thionyl chloride and 0.1 ml of pyridinewere added, and the mixture was stirred for 5 hours. The solvent wasevaporated, and the whole amount of the residue was dissolved in 100 mlof dichloromethane. Ammonia gas was injected into the solution whilestirring. Two hours later, the solution was filtered. The residue wasdissolved in 100 ml of DMF, and 7.9 g of oxalyl chloride was addeddropwise. After further stirring for 1 hour, the mixture was poured ontoiced water. 100 ml of toluene was added, and the organic phase wasseparated. The organic phase was rinsed with water, a saturated aqueoussolution of sodium hydrogencarbonate, and a saturated saline solution,and dried on anhydrous sodium sulfate. The solvent was evaporated, andthe residue was purified by silica gel column chromatography andrecrystallized from ethanol to obtain 9 g white crystals oftrans-2-propyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene.

The following compounds were prepared in the same manner as mentionedabove:

-   trans-2-methyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene,-   trans-2-ethyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene,-   trans-2-butyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene,-   trans-2-pentyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene,-   trans-2-hexyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene,-   trans-2-heptyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene.

Example 10 Synthesis oftrans-2-propyl-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene

20 g oftrans-2-propyl-trans-6-(3-fluoro-4-methoxyphenyl)-trans-decahydronaphthalene(which is a compound obtained in a manner similar to (1-a) except that1-bromo-3-fluro-4-methoxybenzene was used instead of1-bromo-3,5-difluorobenzene) was added to a mixture of 100 ml of aceticacid and 100 ml of 48% aqueous solution of hydrobromic acid, and themixture was heated for 20 hours under refluxing. The temperature wasreduced to room temperature. Water and toluene were added to themixture, and the organic phase was separated. The organic phase wasrinsed with a saturated aqueous solution of sodium hydrogencarbonate,water, and a saturated saline solution, and dried on anhydrous sodiumsulfate. The solvent was evaporated, and the whole amount of the residuewas dissolved in 100 ml of dichloromethane. 19.7 g oftrifluromenthanesulfonic anhydride was added to the solution, and themixture was cooled to 5° C. While the mixture was stirred forcefully, 12ml of pyridine was added dropwise, and thereafter the mixture wasfurther stirred for 1 hour. Water was added to stop the reaction. Theorganic phase was separated out, and the aqueous phase was extractedwith dichloromethane. Organic phases were combined, and the combinedorganic phase was rinsed with 10% hydrochloric acid, a saturated aqueoussolution of sodium hydrogencarbonate, water, and then a saturated salinesolution, and dried on anhydrous sodium sulfate. After the solution waspurified by silica gel column chromatography (hexane), the solvent wasevaporated. The whole amount of the residue was dissolved in 150 ml ofacetonitrile. 1.7 g of dibromobis(triphenylphosphine)nickel(II), 1.4 gof triphenylphosphine, 0.3 g of zinc powder, and 8.5 g of potassiumcyanide were added to the solution, and the mixture was heated at 80° C.for 16 hours while stirring. Water was added to stop the reaction. Theorganic phase was further rinsed with water, and dried on anhydroussodium sulfate. The solution was purified by silica gel columnchromatography (hexane/dichloromethane), and further recrystallized fromethanol to obtain 12.5 g of white solid5-fluoro-6-cyano-2-(trans-4-propylcyclohexyl)naphthalene.

The following compounds were prepared in the same manner as mentionedabove:

-   trans-2-methyl-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene,-   trans-2-ethyl-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene,-   trans-2-butyl-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene,-   trans-2-pentyl-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene,-   trans-2-hexyl-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene,-   trans-2-heptyl-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene,-   trans-2-vinyl-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene,-   trans-2-(1-propenyl)-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene,-   trans-2-(1-pentenyl)-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene,-   trans-2-(3-butenyl)-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene,-   trans-2-(3-pentenyl)-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene.

Example 11 Synthesis oftrans-6-(4-cyano-3,5-difluorophenyl)-trans-2-(1-propenyl)decahydronaphthalene

4.8 ml of a 1.5 M hexane solution of n-butyl lithium was added dropwiseto a 10 ml THF solution of 1.74 g oftrans-6-(3,5-difluorophenyl)-trans-2-(1-propenyl)decahydronaphthalenewhile cooling the solution to −78° C. After stirring for 10 minutes,carbon dioxide was injected into the mixture until saturation. After themixture was left to stand until the temperature reached roomtemperature, 10% hydrochloric acid was added. The organic phase wasextracted using ethyl acetate, rinsed with water, and dried on anhydrousmagnesium sulfate. Then, the solvent was evaporated. 1.9 g of the solidsubstance obtained was suspended in 12 ml of 1,2-ethylene dichloride.1.4 g of thionyl chloride, 0.05 ml of pyridine, and 1 ml ofN,N-dimethylformamide (DMF) were added to the suspension, and themixture was stirred for 1 hour at room temperature. The solvent wasevaporated, and the oily substance obtained was dissolved in 50 ml ofmethylene chloride. Ammonia gas was injected into the solution whilecooling the solution to 10° C. or lower until saturation. After stirringfor 1 hour at room temperature, the solvent was evaporated. 2.6 g of thesolid substance obtained was suspended in 20 ml of DMF. 1.5 ml ofphosphorus oxychloride was added to the suspension while cooling thesuspension to 10° C. or lower, and the mixture was stirred for 1 hour atroom temperature. Water was added to the mixture. The organic phase wasextracted using toluene, rinsed with a saturated saline solution, anddried on anhydrous sodium sulfate. Then, the solvent was evaporated. Theresidue was purified by silica gel column chromatography (hexane), andrecrystallized (ethanol) to obtain 0.3 g of white solidtrans-6-(4-cyano-3,5-difluorophenyl)-trans-2-(1-propenyl)decahydronaphthalene(I-12).

The following compounds were prepared in the same manner as mentionedabove:

-   trans-2-vinyl-trans-6-(4-cyano-3,5-difluorophenyl)-trans-decahydronaphthalene,-   trans-2-(1-propenyl)-trans-6-(4-cyano-3,5-difluorophenyl)-trans-decahydronaphthalene,-   trans-2-(1-pentenyl)-trans-6-(4-cyano-3,5-difluorophenyl)-trans-decahydronaphthalene,-   trans-2-(3-butenyl)-trans-6-(4-cyano-3,5-difluorophenyl)-trans-decahydronaphthalene,-   trans-2-(3-pentenyl)-trans-6-(4-cyano-3,5-difluorophenyl)-trans-decahydronaphthalene.

Example 12 Synthesis oftrans-6-propyl-2-[2-(3,4,5-trifluorophenyl)ethyl]-trans-decahydronaphthalene

(12-a) Synthesis of 6-propyl-trans-decahydronaphthalene-2-carbaldehyde

A 100 ml THF solution of 24 g of6-propyl-trans-decahydro-2-naphthalenone was added dropwise to a Wittigreagent prepared from 38 g of methoxymethyltriphenylphosphonium chlorideand 14 g of potassium t-butoxide in 200 ml of THF, while the mixture wascooled 10° C. or lower. The temperature was reduced to room temperature.After the mixture was stirred for 4 hours, water and hexane were added.The organic phase was separated and rinsed with water, and the solventwas evaporated. The pale yellow oily substance obtained was dissolved in180 ml of THF. 180 ml of 10% hydrochloric acid was added to thesolution, and the mixture was heated for 3 hours under refluxing. Thetemperature was reduced to room temperature, the organic phase wasseparated, and the aqueous phase was extracted with ethyl acetate.Organic phases were combined, the combined organic phase was rinsed witha saturated aqueous solution of sodium hydrogencarbonate, water, and asaturated saline solution, in sequence, and the solvent was evaporated.The pale yellow solid substance obtained was dissolved in 160 ml ofmethanol. 20 ml of 10% aqueous solution of sodium hydroxide was added tothe solution while cooling the solution to 10° C. or lower. Afterstirring the mixture for 2 hours, the temperature was reduced to roomtemperature, and the solvent was evaporated. The pale yellow solidsubstance obtained was rinsed with water, and recrystallized from ahexane solution to obtain 18 g of white solid6-propyl-trans-decahydronaphthalene-2-carbaldehyde.

(12-b) Synthesis of2-[2-(3,4,5-trifluorophenyl)ethenyl]-6-propyl-trans-decahydronaphthalene

A 90 ml THF solution of 18 g of6-propyl-trans-decahydronaphthalene-2-carbaldehyde, which was obtainedin (12-a), was added dropwise to a Wittig reagent prepared from 49 g of3,4,5-trifluorobenzyltriphenylphosphonium bromide and 12 g of potassiumt-butoxide in 250 ml of THF, while the mixture was cooled to 10° C. orlower. The temperature was reduced to room temperature. After themixture was stirred for 4 hours, water and hexane were added. Theorganic phase was separated and rinsed with water, and the solvent wasevaporated. The residue was purified by silica gel column chromatography(hexane) to obtain 22 g of2-[2-(3,4,5-trifluorophenyl)ethenyl]-6-propyl-trans-decahydronaphthaleneas a colorless oily substance.

(1-c) Synthesis oftrans-6-propyl-2-[2-(3,4,5-trifluorophenyl)ethyl]-trans-decahydronaphthalene

22 g of2-[2-(3,4,5-trifluorophenyl)ethenyl]-6-propyl-trans-decahydronaphthalene,which was obtained in (12-b), was dissolved in 120 ml of ethyl acetate.5 g of carbon with 5% palladium was added to the solution. Hydrogenationwas carried out at room temperature for 6 hours. The catalyst wasremoved by way of filtration through celite, and the solvent wasevaporated. The residue was purified by silica gel column chromatography(hexane), and recrystallized from ethanol at −70° C. or lower to obtain6 g of white solidtrans-6-propyl-2-[2-(3,4,5-trifluorophenyl)ethyl]-trans-decahydronaphthalene.

The following compounds were prepared in the same manner as mentionedabove:

-   trans-6-propyl-2-[2-(3,5-difluorophenyl)ethyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[2-(4-fluorophenyl)ethyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[2-(3,4-difluorophenyl)ethyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[2-(4-trifluoromethoxyphenyl)ethyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[2-(3-fluoro-4-trifluoromethoxyphenyl)ethyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[2-(3,5-difluoro-4-trifluoromethoxyphenyl)ethyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[2-(4-difluoromethoxyphenyl)ethyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[2-(3-fluoro-4-difluoromethoxyphenyl)ethyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[2-(3,5-difluoro-4-difluoromethoxyphenyl)ethyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[2-(4-chlorophenyl)ethyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[2-(3-fluoro-4-chlorophenyl)ethyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[2-(3,5-difluoro-4-chlorophenyl)ethyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[2-(4-methoxyphenyl)ethyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[2-(3-fluoro-4-methoxyphenyl)ethyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[2-(3,5-difluoro-4-methoxyphenyl)ethyl]-trans-decahydronaphthalene.

Example 13 Synthesis of4-cyano-3-fluorophenyl-6-pentyl-trans-decahydronaphthalene-2-carboxylate(I-14)

(13-a) Synthesis of 6-pentyl-trans-decahydronaphthalene-2-carbaldehyde

Reaction of 28 g of 6-propyl-trans-decahydro-2-naphthalenone with aWittig reagent similar to that used in (1-a) was carried out to obtain19 g of white solid 6-pentyl-trans-decahydronaphthalene-2-carbaldehyde.

(13-b) Synthesis of 6-pentyl-trans-decahydronaphthalene-2-carboxylicacid

19 g of 6-pentyl-trans-decahydronaphthalene-2-carbaldehyde, which wasobtained in (13-a), was added dropwise to a 60 ml aqueous solution of 12g of concentrated sulfuric acid and 6 g of potassium permanganate whilethe mixture was cooled to 10° C. or lower. After stirring the mixturefor 30 minutes at room temperature, water and ethyl acetate were added.The organic phase was separated and rinsed with water, a saturatedaqueous solution of sodium hydrogencarbonate, water, and a saturatedsaline solution, in sequence. After the organic phase was dried onanhydrous sodium sulfate, the solvent was evaporated. The residue wasrecrystallized from a hexane solution to obtain 8 g white solid6-pentyl-trans-decahydronaphthalene-2-carboxylic acid.

(13-c) Synthesis of4-cyano-3-fluorophenyl-6-pentyl-trans-decahydronaphthalene-2-carboxylate

8 g of 6-pentyl-trans-decahydronaphthalene-2-carboxylic acid, which wasobtained in (13-b), was dissolved in 40 ml of 1,2-dichloroethane. 5 g ofthionyl chloride, 0.1 ml of pyridine, and 5 ml of DMF were added to thesolution, and the mixture was heated for 1 hour under refluxing. Afterexcessive thionyl chloride was evaporated, 50 ml of dichloromethane wasadded, then 4 g of 3-fluoro-4-cyanophenol and 3 g of pyridine wereadded, and the mixture was stirred for 8 hours at room temperature. 10%hydrochloric acid was added, and the organic phase was separated andrinsed with a saturated aqueous solution of sodium hydrogencarbonate anda saturated saline solution, in sequence, and dried on anhydrous sodiumsulfate. After the solvent was evaporated, the residue was purified bysilica gel chromatography (hexane/ethyl acetate), and recrystallizedfrom ethanol to obtain 3 g white crystals of 4-cyano-3-fluorophenyl6-pentyl-trans-decahydronaphthalene-2-carboxylate.

Example 14 Synthesis of 4-cyano-3,5-difluorophenyl6-propyl-trans-decahydronaphthalene-2-carboxylate (I-13)

In a manner similar that in (13-c), esterification reaction of 15 g of6-propyl-trans-decahydronaphthalene-2-carboxylic acid, which wasobtained in (13-b), with 11 g of 3,5-difluoro-4-cyanophenol was carriedout to obtain 6 g of white solid4-cyano-3,5-difluorophenyl-6-propyl-trans-decahydronaphthalene-2-carboxylate.

Example 15 Synthesis of6-(4-vinyl-trans-cyclohexyl)-2-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene(I-15)

(15-a) Synthesis of4-[2-(3,5-difluorophenyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalen-6-yl]cyclohexanoneethyleneacetal

Reaction of 29 g of4-[6-oxo-trans-octahydronaphthalen-2-yl]cyclohexanone monoethyleneacetalwith a Grignard reagent prepared from 3,5-difluoro-1-bromobenzene wascarried out, and dehydration and re-acetalization were carried out toobtain 33 g of pale yellow solid4-[2-(3,5-difluorophenyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalen-6-yl]cyclohexanoneethyleneacetal.

(15-b) Synthesis of4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanoneethyleneacetal

Catalytic hydrogenation reduction of 33 g of4-[2-(3,5-difluorophenyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalen-6-yl]cyclohexanoneethyleneacetal, which was obtained in (15-a), was carried out to obtain29 g of pale yellow solid4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanoneethyleneacetal.

(15-c) Synthesis of4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanone

Deacetalization of 29 g of4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanoneethyleneacetal, which was obtained in (5-b), was carried out to obtain20 g of pale yellow solid4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanone.

(15-d) Synthesis of4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexylcarbaldehyde

Reaction of 20 g of4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanone,which was obtained in (5-c), with a Wittig reagent was carried out toobtain 18 g of pale yellow solid4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanecarbaldehyde.

(15-e) Synthesis of6-(3,5-difluorophenyl)-2-(4-vinyl-trans-cyclohexyl)-trans-decahydronaphthalene

Reaction of 18 g of4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanecarbaldehyde,which was obtained in (15-d), was carried out to obtain 16 g of whitesolid6-(3,5-difluorophenyl)-2-(4-vinyl-trans-cyclohexyl)-trans-decahydronaphthalene.

(15-f) Synthesis of3,5-difluoro-4-[6-(4-vinyl-trans-cyclohexyl)-trans-decahydronaphthalen-2-yl]benzoicacid

Reaction of 16 g of6-(3,5-difluorophenyl)-2-(4-vinyl-trans-cyclohexyl)-trans-decahydronaphthalene,which was obtained in (15-e), with butyl lithium was carried out, andthereafter reaction of the resultant with carbon dioxide was carried outto obtain 16 g of milky-white solid3,5-difluoro-4-[6-(4-vinyl-trans-cyclohexyl)-trans-decahydronaphthalen-2-yl]benzoicacid.

(15-g) Synthesis of6-(4-vinyl-trans-cyclohexyl)-2-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene

16 g of3,5-difluoro-4-[6-(4-vinyl-trans-cyclohexyl)-trans-decahydronaphthalen-2-yl]benzoicacid, which was obtained in (15-f), was dissolved in 80 ml of1,2-dichloroethane. 6 g of thionyl chloride, 0.1 ml of pyridine, and 3ml of DMF were added to the solution, and the mixture was stirred for 6hours at room temperature. After the solvent and excessive thionylchloride were evaporated, 120 ml of dichloromethane was added, andammonia gas was injected while the mixture was cooled to 0° C. Whengeneration of heat stopped, the mixture was stirred for 2 hours at roomtemperature, and crystals which precipitated were separated byprecipitation. The yellow crystals obtained were dissolved in 140 ml ofDMF. 11 g of oxalyl chloride was added dropwise to the solution whilethe mixture was cooled to 0° C. After stirring for 1 hour at roomtemperature, the mixture was poured onto iced water, and extraction wascarried out using toluene. The organic phase was rinsed with water, asaturated aqueous solution of sodium hydrogencarbonate, water, and asaturated saline solution, in sequence, and dried on anhydrous sodiumsulfate. The solvent was evaporated, and the residue was purified bysilica gel column chromatography (toluene) and recrystallized fromethanol to obtain 3 g white crystals of6-(4-vinyl-trans-cyclohexyl)-2-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene.

The following compounds were prepared in the same manner as mentionedabove:

-   6-(trans-1-propenyl)-2-[trans-4-[3,5-difluoro-4-(trans-2-butenyloxy)phenyl]cyclohexyl]-trans-decahydronaphthalene,-   6-(trans-3-butenyl)-2-[trans-4-[3,5-difluoro-4-(trans-2-butenyloxy)phenyl]cyclohexyl]-trans-decahydronaphthalene,-   6-(trans-3-pentenyl)-2-[trans-4-[3,5-difluoro-4-(trans-2-butenyloxy)phenyl]cyclohexyl]-trans-decahydronaphthalene,-   6-(trans-1-pentenyl)-2-[trans-4-[3,5-difluoro-4-(trans-2-butenyloxy)phenyl]cyclohexyl]-trans-decahydronaphthalene.

Example 16 Synthesis oftrans-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene(I-20)

(16-a) Synthesis of trans-2-phenyl-6-pentyl-trans-decahydronaphthalene

To a suspension of 23.6 g of metal magnesium in 90 ml of THF, a 700 mlTHF solution of 150 g of bromobenzene was added dropwise to obtain aGrignard reagent. A 400 ml THF solution of 217 g of6-pentyl-trans-decahydro-2-naphthalenone was added dropwise to thereagent over a period of 30 minutes. After further stirring for 2 hours,400 ml of 10% hydrochloric acid was added. Then, the organic phase wasseparated, rinsed with water, and dried on anhydrous magnesium sulfate.Then, the solvent was evaporated. 261 g of the oily substance obtainedwas dissolved in 800 ml of toluene. 13 g of p-toluenesulfonic acidmonohydrate was added to the solution, and the mixture was heated for 4hours under refluxing using an apparatus equipped with a water separatoruntil evaporation of water stopped. Then, the solution was cooled toroom temperature. Water was added to the solution, and the organic phasewas separated, rinsed with a saturated saline solution, and dried onanhydrous magnesium sulfate. Then, the solvent was evaporated. 240 g ofthe oily substance obtained was dissolved in 1 l of ethyl acetate in anautoclave. 24 g of carbon with 5% palladium was added to the solution.Catalytic hydrogenation reduction was carried out for 5 hours at roomtemperature. Then, the solution was filtered through celite to separatethe catalyst, and the solvent was evaporated to obtain 207 g ofcis/trans mixture of 2-phenyl-6-pentyl-trans-decahydronaphthalene. Thewhole amount of this mixture was dissolved in 630 ml of DMF. 45 g ofpotassium t-butoxide was added to the solution, and the mixture washeated for 2 hours under refluxing. The mixture was cooled to roomtemperature, water was added to the mixture, and extraction was carriedout using hexane. The organic phase was rinsed with a saturated salinesolution, and dried on anhydrous sodium sulfate. The solvent wasevaporated, and the residue was purified by silica gel columnchromatography (hexane) and recrystallized from ethanol to obtain 24white crystals of trans-2-phenyl-6-pentyl-trans-decahydronaphthalene.

The following compounds were prepared in the same manner as mentionedabove:

-   trans-2-phenyl-6-methyl-trans-decahydronaphthalene,-   trans-2-phenyl-6-ethyl-trans-decahydronaphthalene,-   trans-2-phenyl-6-propyl-trans-decahydronaphthalene,-   trans-2-phenyl-6-butyl-trans-decahydronaphthalene,-   trans-2-phenyl-6-hexyl-trans-decahydronaphthalene,-   trans-2-phenyl-6-heptyl-trans-decahydronaphthalene,-   trans-2-(4-chlorophenyl)-6-methyl-trans-decahydronaphthalene,-   trans-2-(4-chlorophenyl)-6-ethyl-trans-decahydronaphthalene,-   trans-2-(4-chlorophenyl)-6-propyl-trans-decahydronaphthalene,-   trans-2-(4-chlorophenyl)-6-butyl-trans-decahydronaphthalene,-   trans-2-(4-chlorophenyl)-6-pentyl-trans-decahydronaphthalene,-   trans-2-(4-chlorophenyl)-6-hexyl-trans-decahydronaphthalene,-   trans-2-(4-chlorophenyl)-6-heptyl-trans-decahydronaphthalene,-   trans-2-(4-methoxyphenyl)-6-methyl-trans-decahydronaphthalene,-   trans-2-(4-methoxyphenyl)-6-ethyl-trans-decahydronaphthalene,-   trans-2-(4-methoxyphenyl)-6-propyl-trans-decahydronaphthalene,-   trans-2-(4-methoxyphenyl)-6-butyl-trans-decahydronaphthalene,-   trans-2-(4-methoxyphenyl)-6-pentyl-trans-decahydronaphthalene,-   trans-2-(4-methoxyphenyl)-6-hexyl-trans-decahydronaphthalene,-   trans-2-(4-methoxyphenyl)-6-heptyl-trans-decahydronaphthalene,-   trans-2-(4-hydroxyphenyl)-6-methyl-trans-decahydronaphthalene,-   trans-2-(4-hydroxyphenyl)-6-ethyl-trans-decahydronaphthalene,-   trans-2-(4-hydroxyphenyl)-6-propyl-trans-decahydronaphthalene,-   trans-2-(4-hydroxyphenyl)-6-butyl-trans-decahydronaphthalene,-   trans-2-(4-hydroxyphenyl)-6-pentyl-trans-decahydronaphthalene,-   trans-2-(4-hydroxyphenyl)-6-hexyl-trans-decahydronaphthalene,-   trans-2-(4-hydroxyphenyl)-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-(3-fluorophenyl)-6-methyl-trans-decahydronaphthalene,-   trans-2-(3-fluorophenyl)-6-ethyl-trans-decahydronaphthalene,-   trans-2-(3-fluorophenyl)-6-propyl-trans-decahydronaphthalene,-   trans-2-(3-fluorophenyl)-6-butyl-trans-decahydronaphthalene,-   trans-2-(3-fluorophenyl)-6-pentyl-trans-decahydronaphthalene,-   trans-2-(3-fluorophenyl)-6-hexyl-trans-decahydronaphthalene,-   trans-2-(3-fluorophenyl)-6-heptyl-trans-decahydronaphthalene,-   trans-2-(3,5-difluorophenyl)-6-methyl-trans-decahydronaphthalene,-   trans-2-(3,5-difluorophenyl)-6-ethyl-trans-decahydronaphthalene,-   trans-2-(3,5-difluorophenyl)-6-propyl-trans-decahydronaphthalene,-   trans-2-(3,5-difluorophenyl)-6-butyl-trans-decahydronaphthalene,-   trans-2-(3,5-difluorophenyl)-6-pentyl-trans-decahydronaphthalene,-   trans-2-(3,5-difluorophenyl)-6-hexyl-trans-decahydronaphthalene,-   trans-2-(3,5-difluorophenyl)-6-heptyl-trans-decahydronaphthalene,-   trans-2-(4-iodophenyl)-6-pentyl-trans-decahydronaphthalene,-   trans-2-phenyl-6-pentyl-trans-decahydronaphthalene.    (16-b) Synthesis of    trans-2-(4-iodophenyl)-6-pentyl-trans-decahydronaphthalene

227 g of trans-2-phenyl-6-pentyl-trans-decahydronaphthalene, which wasobtained in (16-a), was dissolved in 80 ml of 1,2-dichloroethane and 670ml of acetic acid. 125 g of iodine and 91 g of orthoperiodic acid wereadded, and then 180 ml of 10% sulfuric acid was added. After the mixturewas heated for 1.5 hours under refluxing, the mixture was cooled to roomtemperature, and extraction was carried out using toluene. Then, theorganic phase was rinsed with a saturated aqueous solution of sodiumhydrogensulfite and a saturated saline solution, in sequence, and driedon anhydrous magnesium sulfate. After the solvent was evaporated, theresidue was recrystallized from ethanol/toluene to obtain 254 g whitecrystals of trans-2-(4-iodophenyl)-6-pentyl-trans-decahydronaphthalene.

(16-c) Synthesis oftrans-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene

25 g of trans-2-(4-iodophenyl)-6-pentyl-trans-decahydronaphthalene,which was obtained in (16-b), was dissolved in a mixed solution of 48 mlof toluene and 24 ml of ethanol. 0.8 g oftetrakis(triphenylphosphine)palladium(0) and 48 ml aqueous solution of 2M sodium carbonate were added to the mixture, and 32 ml ethanol solutionof 16 g of 3,4,5-trifluorophenylboric acid was further added dropwiseover a period of 10 minutes. After heating the mixture for 24 hours at70° C. while stirring, the mixture was cooled to room temperature, andwater was added to the mixture. After extraction was carried out usingtoluene, the organic phase was rinsed with a saline solution and driedon anhydrous magnesium sulfate. After the solvent was evaporated, theresidue was purified by silica gel column chromatography (hexane) andrecrystallized from ethanol to obtain 18 g white crystals oftrans-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene.

The following compounds were prepared in the same manner as mentionedabove:

-   trans-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(3,4-difluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(3,4-difluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(3,4-difluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(3,4-difluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(3,4-difluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(3,4-difluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3,4-difluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(4-fluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(4-fluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(4-fluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(4-fluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(4-fluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(4-fluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(4-fluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(4-chlorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(4-chlorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(4-chlorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(4-chlorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(4-chlorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(4-chlorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(4-chlorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(4-trifluoromethylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(4-trifluoromethylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(4-trifluoromethylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(4-trifluoromethylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(4-trifluoromethylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(4-trifluoromethylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(4-trifluoromethylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(4-methoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(4-methoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(4-benzyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(4-benzyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-benzyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-benzyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(4-ethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(4-ethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(4-ethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(4-ethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(4-ethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(4-ethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(4-ethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4    (2,3-difluoro-4-ethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(2,3-difluoro-4-ethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(2,3-difluoro-4-ethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(2,3-difluoro-4-ethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(2,3-difluoro-4-ethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(2,3-difluoro-4-ethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(2,3-difluoro-4-ethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(4-allyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(4-allyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(4-allyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(4-allyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(4-allyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(4-allyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(4-allyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(4-methylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(4-methylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(4-methylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(4-methylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(4-methylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(4-methylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(4-methylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(4-ethylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(4-ethylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(4-ethylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(4-ethylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(4-ethylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(4-ethylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(4-ethylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-(4-propylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-(4-propylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-(4-propylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-(4-propylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-(4-propylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-(4-propylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-(4-propylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3-fluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene.

Example 17 Synthesis oftrans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene(I-21)

(17-a) Synthesis oftrans-2-(3,5-difluoro-4-iodophenyl)-6-propyl-trans-decahydronaphthalene

50 ml of 1.5 M hexane solution of n-butyl lithium was added dropwise toa 100 ml THF solution of 17 g oftrans-2-(3,5-difluorophenyl)-6-propyl-trans-decahydronaphthalene, whichwas cooled to −45° C., over a period of 10 minutes. After stirring themixture for 30 minutes, the temperature was increased to roomtemperature, and water was added. A 10% aqueous solution of sodiumhydrogen sulfite was added until the color of iodine was not observed.The organic phase was extracted using hexane, rinsed with a saturatedsaline solution, and dried on anhydrous magnesium sulfate. Then, thesolvent was evaporated to obtain 23 g of white solidtrans-2-(3,5-difluoro-4-iodophenyl)-6-propyl-trans-decahydronaphthalene.

(17-b) Synthesis oftrans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene

23 g oftrans-2-(3,5-difluoro-4-iodophenyl)-6-propyl-trans-decahydronaphthalene,which was obtained in (17-a), was dissolved in a mixed solution of 38 mlof toluene and 20 ml of ethanol. 1.2 g oftetrakis(triphenylphosphine)palladium(0) and 37 ml aqueous solution of 2M sodium carbonate were added to the mixture, and 10 ml ethanol solutionof 11 g of 3,4-difluorophenylboric acid was further added dropwise overa period of 10 minutes. After heating the mixture for 18 hours at 70° C.while stirring, the mixture was cooled to room temperature, and waterwas added to the mixture. After extraction was carried out usingtoluene, the organic phase was rinsed with a saline solution and driedon anhydrous magnesium sulfate. After the solvent was evaporated, theresidue was purified by silica gel column chromatography andrecrystallized three times from ethanol to obtain 11 g white crystals oftrans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene.

The following compounds were prepared in the same manner as mentionedabove:

-   trans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6—propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-ethylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-ethylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-ethylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-ethylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-ethylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-ethylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-ethylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-propylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-propylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-propylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-propylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-propylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-propylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-propylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-benzyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-benzyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene,-   trans-2-[3,5-difluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene.

Example 18 Synthesis of4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoic acid

28 g oftrans-2-[4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-trans-propyldecahydronaphthalenewas dissolved in 140 ml of THF. The solution was heated for 4 hoursunder refluxing, and then the temperature was reduced to roomtemperature. The organic phase was separated, rinsed with a saturatedsaline solution and dried on anhydrous magnesium sulfate. Then, thesolvent was evaporated to obtain 23 g of4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoic acid

The following compounds were prepared in the same manner as mentionedabove:

-   4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoic acid,-   4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoic acid,-   4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoic acid,-   4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoic acid,-   4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoic acid,-   4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoic acid,-   3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoic    acid,-   3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoic    acid,-   3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoic    acid,-   3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoic    acid,-   3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoic    acid,-   3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoic    acid,-   3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoic    acid.

Example 19 Synthesis of 3-fluoro-4-cyanophenyl4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate

22 g of 4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoic acid,which was obtained in Example 18, was dissolved in 110 ml ofdichloromethane. 17 g of thionyl chloride, 0.1 ml of pyridine, and 10 mlof DMF were added to the solution, and the mixture was heated for 1 hourunder refluxing. After excessive thionyl chloride was evaporated, 110 mlof dichloromethane was added, then 10 g of 3-fluoro-4-cyanophenol and 10g of pyridine were added, and the mixture was stirred for 8 hours atroom temperature. 10% hydrochloric acid was added, and the organic phasewas separated and rinsed with a saturated aqueous solution of sodiumhydrogencarbonate and a saturated saline solution, in sequence, anddried on anhydrous sodium sulfate. After the solvent was evaporated, theresidue was purified by silica gel chromatography (hexane/ethylacetate), and recrystallized from ethanol to obtain 23 g white crystalsof 3-fluoro-4-cyanophenyl4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate.

The following compounds were prepared in the same manner as mentionedabove:

-   3-fluoro-4-cyanophenyl    4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    3,5-difluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    3,5-difluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    3,5-difluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    3,5-difluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    3,5-difluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    3,5-difluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-fluoro-4-cyanophenyl    3,5-difluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    3,5-difluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    3,5-difluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    3,5-difluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    3,5-difluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    3,5-difluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    3,5-difluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-cyanophenyl    3,5-difluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    3,5-difluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    3,5-difluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    3,5-difluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    3,5-difluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    3,5-difluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    3,5-difluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,5-difluoro-4-cyanophenyl    3,5-difluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-fluorophenyl    3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-fluorophenyl    3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-fluorophenyl    3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-fluorophenyl    3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-fluorophenyl    3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-fluorophenyl    3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-fluorophenyl    3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-trifluoromethoxyphenyl    3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-trifluoromethoxyphenyl    3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-trifluoromethoxyphenyl    3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-trifluoromethoxyphenyl    3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-trifluoromethoxyphenyl    3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-trifluoromethoxyphenyl    3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-trifluoromethoxyphenyl    3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-trifluoromethylphenyl    3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-trifluoromethylphenyl    3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-trifluoromethylphenyl    3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-trifluoromethylphenyl    3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-trifluoromethylphenyl    3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-trifluoromethylphenyl    3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-trifluoromethylphenyl    3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,4-difluorophenyl    3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,4-difluorophenyl    3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,4-difluorophenyl    3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,4-difluorophenyl    3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,4-difluorophenyl    3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,4-difluorophenyl    3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,4-difluorophenyl    3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,4,5-trifluorophenyl    3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,4,5-trifluorophenyl    3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,4,5-trifluorophenyl    3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,4,5-trifluorophenyl    3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,4,5-trifluorophenyl    3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,4,5-trifluorophenyl    3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   3,4,5-trifluorophenyl    3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-methylphenyl    3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-methylphenyl    3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   3-4-methylphenyl    fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-methylphenyl    3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-methylphenyl    3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-methylphenyl    3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-methylphenyl    3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-ethylphenyl    3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-ethylphenyl    3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-ethylphenyl    3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-ethylphenyl    3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-ethylphenyl    3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-ethylphenyl    3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-ethylphenyl    3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-methoxyphenyl    3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-methoxyphenyl    3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-methoxyphenyl    3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-methoxyphenyl    3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-methoxyphenyl    3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-methoxyphenyl    3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-methoxyphenyl    3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-(3-butenyl)phenyl    3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate.,-   4-(3-butenyl)phenyl    3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-(3-butenyl)phenyl    3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-(3-butenyl)phenyl    3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-(3-butenyl)phenyl    3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-(3-butenyl)phenyl    3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-(3-butenyl)phenyl    3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-phenyl    3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-phenyl    3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-phenyl    3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-phenyl    3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-phenyl    3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-phenyl    3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-phenyl    3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-chlorophenyl    3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-chlorophenyl    3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-chlorophenyl    3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-chlorophenyl    3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-chlorophenyl    3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-chlorophenyl    3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-chlorophenyl    3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-allyloxyphenyl    3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-allyloxyphenyl    3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-allyloxyphenyl    3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-allyloxyphenyl    3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-allyloxyphenyl    3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-allyloxyphenyl    3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-allyloxyphenyl    3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate.

Example 20 Synthesis of6-(1,2-difluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene(I-27)

(20-a) Synthesis of6-(1,2-difluoronaphthalen-6-yl)-2-propyl-trans-1,2,3,4,7,8,9,10-octahydronaphthalene

Reaction of 12 g of 6-propyldecahydro-2-naphthalenone with a Grignardreagent prepared from 1,2-difluoro-6-bromonaphthalene and dehydrationwere carried out to obtain 15 g of pale yellow liquid6-(1,2-difluoronaphthalen-6-yl)-2-propyl-trans-1,2,3,4,7,8,9,10-octahydronaphthalene.

(20-b) Synthesis of6-(1,2-difluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene

Catalytic hydrogenation reduction and isomerization of 15 g of6-(1,2-difluoronaphthalen-6-yl)-2-propyl-trans-1,2,3,4,7,8,9,10-octahydronaphthalene,which was obtained in (20-a), were carried out to obtain 3 g of whitesolid6-(1,2-difluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene.

The following compounds were prepared in the same manner as mentionedabove:

-   6-(2-fluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(2-fluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(2-fluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(2-fluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(2-fluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(2-fluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(2-fluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,2-difluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,2-difluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,2-difluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,2-difluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,2-difluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,2-difluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(2,3-difluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(2,3-difluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(2,3-difluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(2,3-difluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(2,3-difluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(2,3-difluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(2,3-difluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,2,3-trifluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,2,3-trifluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,2,3-trifluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,2,3-trifluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,2,3-trifluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,2,3-trifluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,2,3-trifluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,7-difluoronaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,7-difluoronaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,7-difluoronaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,7-difluoronaphthalen-3-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,7-difluoronaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,7-difluoronaphthalen-3-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,7-difluoronaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,2,8-trifluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,2,8-trifluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,2,8-trifluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,2,8-trifluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,2,8-trifluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,2,8-trifluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,2,8-trifluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,6,7-trifluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,6,7-trifluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,6,7-trifluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,6,7-trifluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,6,7-trifluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,6,7-trifluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,6,7-trifluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,2,3,8-tetrafluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,2,3,8-tetrafluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,2,3,8-tetrafluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,2,3,8-tetrafluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,2,3,8-tetrafluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,2,3,8-tetrafluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,2,3,8-tetrafluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(2-trifluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(2-trifluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(2-trifluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(2-trifluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(2-trifluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(2-trifluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(2-trifluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-trifluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-trifluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-trifluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-trifluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-trifluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-trifluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-trifluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(2-trifluoromethoxy-3-fluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(2-trifluoromethoxy-3-fluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(2-trifluoromethoxy-3-fluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(2-trifluoromethoxy-3-fluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(2-trifluoromethoxy-3-fluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(2-trifluoromethoxy-3-fluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(2-trifluoromethoxy-3-fluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,3-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,3-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,3-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,3-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,3-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,3-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,3-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-trifluoromethoxynaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-trifluoromethoxynaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-trifluoromethoxynaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-trifluoromethoxynaphthalen-3-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-trifluoromethoxynaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-trifluoromethoxynaphthalen-3-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-trifluoromethoxynaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-trifluoromethoxynaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-trifluoromethoxynaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-trifluoromethoxynaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-trifluoromethoxynaphthalen-3-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-trifluoromethoxynaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-trifluoromethoxynaphthalen-3-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-trifluoromethoxynaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(2-difluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(2-difluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(2-difluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(2-difluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(2-difluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(2-difluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(2-difluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-difluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-difluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-difluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-difluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-difluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-difluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-difluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(2-difluoromethoxy-3-fluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(2-difluoromethoxy-3-fluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(2-difluoromethoxy-3-fluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(2-difluoromethoxy-3-fluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(2-difluoromethoxy-3-fluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(2-difluoromethoxy-3-fluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(2-difluoromethoxy-3-fluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,3-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,3-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,3-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,3-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,3-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,3-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,3-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-difluoromethoxynaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-difluoromethoxynaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-difluoromethoxynaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-difluoromethoxynaphthalen-3-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-difluoromethoxynaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-difluoromethoxynaphthalen-3-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-difluoromethoxynaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-difluoromethoxynaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-difluoromethoxynaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-difluoromethoxynaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-difluoromethoxynaphthalen-3-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-difluoromethoxynaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-difluoromethoxynaphthalen-3-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-difluoromethoxynaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(2-chloronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(2-chloronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(2-chloronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(2-chloronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(2-chloronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(2-chloronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(2-chloronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-chloronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-chloronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-chloronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-chloronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-chloronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-chloronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1-fluoro-2-chloronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(2-chloro-3-fluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(2-chloro-3-fluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(2-chloro-3-fluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(2-chloro-3-fluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(2-chloro-3-fluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(2-chloro-3-fluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(2-chloro-3-fluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(2-chloro-1,3-difluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(2-chloro-1,3-difluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(2-chloro-1,3-difluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(2-chloro-1,3-difluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(2-chloro-1,3-difluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(2-chloro-1,3-difluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(2-chloro-1,3-difluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-chloronaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-chloronaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-chloronaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-chloronaphthalen-3-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-chloronaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-chloronaphthalen-3-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-chloronaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-7-chloronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-7-chloronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-7-chloronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-7-chloronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(11,8-difluoro-7-chloronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-7-chloronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-7-chloronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-chloronaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-chloronaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-chloronaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-chloronaphthalen-3-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-chloronaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-chloronaphthalen-3-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-chloronaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-7-chloronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-7-chloronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-7-chloronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-7-chloronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-7-chloronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-7-chloronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-7-chloronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(2-cyanonaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(2-cyanonaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(2-cyanonaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(2-cyanonaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(2-cyanonaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(2-cyanonaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(2-cyanonaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(2-cyano-1-fluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(2-cyano-1-fluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(2-cyano-1-fluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(2-cyano-1-fluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(2-cyano-1-fluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(2-cyano-1-fluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(2-cyano-1-fluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(2-cyano-3-fluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(2-cyano-3-fluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(2-cyano-3-fluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(2-cyano-3-fluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(2-cyano-3-fluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(2-cyano-3-fluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(2-cyano-3-fluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(2-cyano-1,3-difluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(2-cyano-1,3-difluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(2-cyano-1,3-difluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(2-cyano-1,3-difluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(2-cyano-1,3-difluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(2-cyano-1,3-difluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(2-cyano-1,3-difluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-cyanonaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-cyanonaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-cyanonaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-cyanonaphthalen-3-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-cyanonaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-cyanonaphthalen-3-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1-fluoro-7-cyanonaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-7-cyanonaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-7-cyanonaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-7-cyanonaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-7-cyanonaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-7-cyanonaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-7-cyanonaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-7-cyanonaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-cyanonaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-cyanonaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-cyanonaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-cyanonaphthalen-3-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-cyanonaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-cyanonaphthalen-3-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-cyanonaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-7-cyanonaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-7-cyanonaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-7-cyanonaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-7-cyanonaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-7-cyanonaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-7-cyanonaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(1,3,8-trifluoro-7-cyanonaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene,-   6-[2-(trifluoromethyl)naphthalen-6-yl]-2-methyl-trans-decahydronaphthalene,-   6-[2-(trifluoromethyl)naphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene,-   6-[2-(trifluoromethyl)naphthalen-6-yl]-2-propyl-trans-decahydronaphthalene,-   6-[2-(trifluoromethyl)naphthalen-6-yl]-2-butyl-trans-decahydronaphthalene,-   6-[2-(trifluoromethyl)naphthalen-6-yl]-2-pentyl-trans-decahydronaphthalene,-   6-[2-(trifluoromethyl)naphthalen-6-yl]-2-hexyl-trans-decahydronaphthalene,-   6-[2-(trifluoromethyl)naphthalen-6-yl]-2-heptyl-trans-decahydronaphthalene,-   6-[1-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-methyl-trans-decahydronaphthalene,-   6-[1-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-ethyl-trans-decahydronaphthalene,-   6-[1-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-propyl-trans-decahydronaphthalene,-   6-[1-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-butyl-trans-decahydronaphthalene,-   6-[1-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-pentyl-trans-decahydronaphthalene,-   6-[1-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-hexyl-trans-decahydronaphthalene,-   6-[1-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-heptyl-trans-decahydronaphthalene,-   6-[3-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-methyl-trans-decahydronaphthalene,-   6-[3-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-ethyl-trans-decahydronaphthalene,-   0.6-[3-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-propyl-trans-decahydronaphthalene,-   6-[3-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-butyl-trans-decahydronaphthalene,-   6-[3-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-pentyl-trans-decahydronaphthalene,-   6-[3-fluoro-2-(trifluoromethyl)naphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene,-   6-[3-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-heptyl-trans-decahydronaphthalene,-   6-[1,3-difluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-methyl-trans-decahydronaphthalene,-   6-[1,3-difluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-ethyl-trans-decahydronaphthalene,-   6-(1,3-difluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-propyl-trans-decahydronaphthalene,-   6-[1,3-difluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-butyl-trans-decahydronaphthalene,-   6-[1,3-difluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-pentyl-trans-decahydronaphthalene,-   6-[1,3-difluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-hexyl-trans-decahydronaphthalene,-   6-[1,3-difluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-heptyl-trans-decahydronaphthalene,-   6-[1-fluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-methyl-trans-decahydronaphthalene,-   6-[1-fluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-ethyl-trans-decahydronaphthalene,-   6-[1-fluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-propyl-trans-decahydronaphthalene,-   6-[1-fluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-butyl-trans-decahydronaphthalene,-   6-[1-fluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-pentyl-trans-decahydronaphthalene,-   6-[1-fluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-hexyl-trans-decahydronaphthalene,-   6-[1-fluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-heptyl-trans-decahydronaphthalene,-   6-[1,8-difluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-methyl-trans-decahydronaphthalene,-   6-[1,8-difluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-ethyl-trans-decahydronaphthalene,-   6-(1,8-difluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-propyl-trans-decahydronaphthalene,-   6-[1,8-difluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-butyl-trans-decahydronaphthalene,-   6-[1,8-difluoro-7-(trifluoromethyl)naphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene,-   6-[1,8-difluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-hexyl-trans-decahydronaphthalene,-   6-[1,8-difluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-heptyl-trans-decahydronaphthalene,-   6-[1,6-difluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-methyl-trans-decahydronaphthalene,-   6-[1,6-difluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-ethyl-trans-decahydronaphthalene,-   6-[1,6-difluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-propyl-trans-decahydronaphthalene,-   6-(1,6-difluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-butyl-trans-decahydronaphthalene,-   6-[1,6-difluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-pentyl-trans-decahydronaphthalene,-   6-[1,6-difluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-hexyl-trans-decahydronaphthalene,-   6-[1,6-difluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-heptyl-trans-decahydronaphthalene,-   6-[1,3,8-trifluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-methyl-trans-decahydronaphthalene,-   6-[1,3,8-trifluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-ethyl-trans-decahydronaphthalene,-   6-[1,3,8-trifluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-propyl-trans-decahydronaphthalene,-   6-[1,3,8-trifluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-butyl-trans-decahydronaphthalene,-   6-[1,3,8-trifluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-pentyl-trans-decahydronaphthalene,-   6-[1,3,8-trifluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-hexyl-trans-decahydronaphthalene,-   6-[1,3,8-trifluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-heptyl-trans-decahydronaphthalene,-   methyl-6-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl-6-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl-6-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl-6-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl-6-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl-6-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl-6-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1-fluoro-6-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1-fluoro-6-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1-fluoro-6-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1-fluoro-6-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1-fluoro-6-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1-fluoro-6-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    l-fluoro-6-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    3-fluoro-6-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    3-fluoro-6-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    3-fluoro-6-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    3-fluoro-6-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    3-fluoro-6-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    3-fluoro-6-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    3-fluoro-6-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,3-difluoro-6-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,3-difluoro-6-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,3-difluoro-6-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,3-difluoro-6-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,3-difluoro-6-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,3-difluoro-6-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,3-difluoro-6-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    l-fluoro-7-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1-fluoro-7-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1-fluoro-7-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    l-fluoro-7-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1-fluoro-7-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1-fluoro-7-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1-fluoro-7-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1,2-difluoro-7-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1,2-difluoro-7-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1,2-difluoro-7-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1,2-difluoro-7-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1,2-difluoro-7-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1,2-difluoro-7-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1,2-difluoro-7-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1-fluoro-3-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    l-fluoro-3-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1-fluoro-3-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   ethyl    1-fluoro-3-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    l-fluoro-3-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1-fluoro-3-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    l-fluoro-3-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,8-difluoro-6-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,8-difluoro-6-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,8-difluoro-6-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,8-difluoro-6-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,8-difluoro-6-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,8-difluoro-6-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,8-difluoro-6-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,6-difluoro-3-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,6-difluoro-3-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   ethyl    1,6-difluoro-3-(6-propyl-trans-decahydronaphthalen-2-l)naphthalene-7-carboxylate,-   methyl    1,6-difluoro-3-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,6-difluoro-3-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,6-difluoro-3-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,6-difluoro-3-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,3,8-trifluoro-6-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,3,8-trifluoro-6-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,3,8-trifluoro-6-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,3,8-trifluoro-6-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,3,8-trifluoro-6-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,3,8-trifluoro-6-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,3,8-trifluoro-6-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    3-fluoro-2-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    3-fluoro-2-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    3-fluoro-2-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    3-fluoro-2-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    3-fluoro-2-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    3-fluoro-2-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    3-fluoro-2-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1,7-difluoro-6-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,7-difluoro-6-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,7-difluoro-6-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,7-difluoro-6-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,7-difluoro-6-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,7-difluoro-6-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,7-difluoro-6-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate,-   methyl    1,2-difluoro-3-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,2-difluoro-3-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,2-difluoro-3-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,2-difluoro-3-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,2-difluoro-3-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,2-difluoro-3-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,2-difluoro-3-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,2,8-trifluoro-3-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,2,8-trifluoro-3-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   15 methyl    1,2,8-trifluoro-3-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,2,8-trifluoro-3-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,2,8-trifluoro-3-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,2,8-trifluoro-3-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   methyl    1,2,8-trifluoro-3-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate,-   25 methyl    1-fluoro-2-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1-fluoro-2-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1-fluoro-2-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1-fluoro-2-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1-fluoro-2-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1-fluoro-2-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1-fluoro-2-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1,7-difluoro-2-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1,7-difluoro-2-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1,7-difluoro-2-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1,7-difluoro-2-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1,7-difluoro-2-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1,7-difluoro-2-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1,7-difluoro-2-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1,8-difluoro-2-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1,8-difluoro-2-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1,8-difluoro-2-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1,8-difluoro-2-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1,8-difluoro-2-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1,8-difluoro-2-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1,8-difluoro-2-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate,-   methyl    1,2,8-trifluoro-7-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1,2,8-trifluoro-7-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1,2,8-trifluoro-7-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1,2,8-trifluoro-7-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1,2,8-trifluoro-7-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1,2,8-trifluoro-7-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate,-   methyl    1,2,8-trifluoro-7-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate.

Example 21 Synthesis of 2,6-bis(3-butenyl)-trans-decahydronaphthalene(I-22)

(21-a) Synthesis of trans-decahydronaphthalen-2,6-dione

21 g of trans-decahydronaphthalen-2,6-dione monoethyleneacetal wasdissolved in 110 ml of toluene. 50 ml of formic acid was added to thesolution, and the mixture was stirred for 1 hour at room temperature.Water was added to the mixture, and the organic phase was separated,rinsed with water, a saturated aqueous solution of sodiumhydrogencarbonate, and a saturated saline solution, in sequence, anddried on anhydrous sodium sulfate. Then, the solvent was evaporated toobtain 16 g of pale yellow solid trans-decahydronaphthalen-2,6-dione.

(21-b) Synthesis of trans-decahydronaphthalene-2,6-dicarbaldehyde

An 80 ml THF solution of 16 g of trans-decahydronaphthalen-2,6-dione,which was obtained in (21-a), was added dropwise to a Wittig reagentprepared from 72 g of methoxymethyltriphenylphosphonium chloride and 26g of potassium t-butoxide in 290 ml of THF, while the mixture was cooledto 10° C. or lower. The temperature was reduced to room temperature.After the mixture was stirred for 4 hours, water and hexane were added.The organic phase was separated and rinsed with water, and the solventwas evaporated. The pale yellow oily substance obtained was dissolved in90 ml of THF. 90 ml of 10% hydrochloric acid was added to the solution,and the mixture was heated for 3 hours under refluxing. The temperaturewas reduced to room temperature, and the organic phase was separated.The aqueous phase was extracted with ethyl acetate. Organic phases werecombined, and rinsed with a saturated aqueous solution of sodiumhydrogencarbonate, water, and a saturated saline solution, in sequence.Then, the solvent was evaporated. The pale yellow solid substanceobtained was dissolved in 85 ml of methanol. 10 ml of 10% aqueoussolution of sodium hydroxide was added to the solution while the mixturewas cooled to 10° C. or lower. After the mixture was stirred for 2.5hours at room temperature, the temperature was reduced to roomtemperature. Then, the solvent was evaporated, and the pale yellow solidsubstance obtained was rinsed with water and recrystallized from ahexane solution to obtain 16 g of white solidtrans-decahydronaphthalene-2,6-dicarbaldehyde.

(21-c) Synthesis of 2,6-bis(3-oxopropyl)-trans-decahydronaphthalene

Reaction of 16 g of trans-decahydronaphthalene-2,6-dicarbaldehyde, whichwas obtained in (21-a), with a Wittig reagent which is similar to thatused in (1-b) was repeated twice to obtain 15 g of pale yellow solid2,6-bis(3-oxopropyl)-trans-decahydronaphthalene.

(21-d) Synthesis of 2,6-bis(3-butenyl)-trans-decahydronaphthalene

An 85 ml THF solution of 15 g of2,6-bis(3-oxopropyl)-trans-decahydronaphthalene, which was obtained in(21-c), was added dropwise to a Wittig reagent prepared from 60 g ofmethyltriphenylphosphonium iodide and 18 g of potassium t-butoxide in300 ml of THF, while the mixture was cooled to 10° C. or lower. Thetemperature was reduced to room temperature. After the mixture wasstirred for 4 hours, water and hexane were added. The organic phase wasseparated and rinsed with water, and the solvent was evaporated. Theresidue was purified by silica gel column chromatography (hexane) toobtain 6 g of 2,6-bis(3-butenyl)-trans-decahydronaphthalene (I-22) acolorless oily substance.

The following compounds were prepared in the same manner as mentionedabove:

-   2,6-bis(3-pentenyl)-trans-decahydronaphthalene,-   2,6-bis(1-pentenyl)-trans-decahydronaphthalene,-   2,6-bis(1-propenyl)-trans-decahydronaphthalene,-   2,6-divinyl-trans-decahydronaphthalene.

Example 22 Synthesis of2-(trans-4-propylcyclohexyl)-6-vinyl-trans-decahydronaphthalene (I-23)

(22-a) Synthesis of6-(trans-4-propylcyclohexyl)-trans-decahydronaphthalene-2-carbaldehyde

Reaction of 28 g of6-(trans-4-propylcyclohexyl)-trans-decahydro-2-naphthalenone with theWittig reagent described above was carried out to obtain 28 g of whitesolid6-(trans-4-propylcyclohexyl)-trans-decahydronaphthalene-2-carbaldehyde.

(22-b) Synthesis of2-(trans-4-propylcyclohexyl)-6-vinyl-trans-decahydronaphthalene

Reaction of 28 g of6-(trans-4-propylcyclohexyl)-trans-decahydronaphthalene-2-carbaldehyde,which was obtained in (22-a), with a Wittig reagent which is similar tothat used in (1-d) was carried out to obtain 10 g of white solid2-(trans-4-propylcyclohexyl)-6-vinyl-trans-decahydronaphthalene (I-4).

The following compound was prepared in the same manner as mentionedabove:

-   2-(trans-4-propylcyclohexyl)-6-(3-butenyl)-trans-decahydronaphthalene.

Example 23 Synthesis of2-(trans-4-propylcyclohexyl)-6-(trans-1-propenyl)-trans-decahydronaphthalene(I-24)

Reaction of 12 g of6-(trans-4-propylcyclohexyl)-trans-decahydronaphthalene-2-carbaldehyde,which was obtained in (22-a), with the Wittig reagent described above,and treatment with benzenesulfinic acid were carried out to obtain 4 gof white solid2-(trans-4-propylcyclohexyl)-6-(trans-1-propenyl)-trans-decahydronaphthalene(I-24).

The following compounds were prepared in the same manner as mentionedabove:

-   2-(trans-4-propylcyclohexyl)-6-(trans-1-pentenyl)-trans-decahydronaphthalene,-   2-(trans-4-propylcyclohexyl)-6-(trans-3-pentenyl)-trans-decahydronaphthalene.

Example 24 Synthesis of2-(trans-4-propylcyclohexyl)-6-(2,2-difluoroethenyl)-trans-decahydronaphthalene(I-25)

To a solution of 8.7 g of6-(trans-4-propylcyclohexyl)decahydronaphthalene-2-carbaldehyde, whichwas obtained in (22-a), and 8.7 g of triphenylphosphine in 10 ml ofdiethyleneglycol dimethylether (Diglyme), the solution being heated at160° C. while stirring, a 20 ml Diglyme solution of 7.1 g of sodiumchlorodifluoroacetate was added dropwise over a period of 30 minutes.After the heating was continued under the same conditions for 2 hours,the mixture was left to cool to room temperature. Water and hexane wereadded to the mixture, and the organic phase was separated, rinsed with10% hydrochloric acid, a saturated aqueous solution of sodium carbonate,and a saturated saline solution, in sequence, and dried on anhydroussodium sulfate. Then, the solvent was evaporated. The residue waspurified by silica gel column chromatography (hexane) and recrystallizedfrom ethanol at 10° C. or lower to obtain 0.6 g of2-(trans-4-propylcyclohexyl)-6-(2,2-difluoroethenyl)-trans-decahydronaphthalene(I-25).

Example 25 Synthesis oftrans-6-propyl-2-[4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene

23 g of trans-6-propyl-2-(4-iodophenyl)-trans-decahydronaphthalene wasdissolved in 45 ml of DMF. 1.3 g oftetrakis(triphenylphosphine)palladium(0), 0.4 g of copper iodide (I),and 6.0 g of (4-methyl)phenylacetylene were added to the mixture. Afterheating the mixture for 2 hours at 50° C. while stirring, the mixturewas cooled to room temperature, and 10% hydrochloric acid was added tothe mixture. After extraction was carried out using toluene, the organicphase was rinsed with a saline solution and dried on anhydrous magnesiumsulfate. After the solvent was evaporated, the residue was purified bysilica gel column chromatography (hexane) and recrystallized once fromethanol to obtain 10 g white crystals oftrans-6-propyl-2-[4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene.

The following compounds were prepared in the same manner as mentionedabove:

-   trans-6-methyl-2-[4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-ethyl-2-[4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-butyl-2-[4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-pentyl-2-[4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-hexyl-2-[4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-heptyl-2-[4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-methyl-2-[3-fluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-ethyl-2-[3-fluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[3-fluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-butyl-2-[3-fluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-pentyl-2-[3-fluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-hexyl-2-[3-fluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-heptyl-2-[3-fluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-methyl-2-[3,5-difluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-ethyl-2-[3,5-difluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[3,5-difluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-butyl-2-[3,5-difluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-pentyl-2-[3,5-difluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-hexyl-2-[3,5-difluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-heptyl-2-[3,5-difluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-methyl-2-[4-(4-ethylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-ethyl-2-[4-(4-ethylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[4-(4-ethylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-butyl-2-[4-(4-ethylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-pentyl-2-[4-(4-ethylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-hexyl-2-[4-(4-ethylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-heptyl-2-[4-(4-ethylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-methyl-2-[4-(4-propylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-ethyl-2-[4-(4-propylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[4-(4-propylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-butyl-2-[4-(4-propylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-pentyl-2-[4-(4-propylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-hexyl-2-[4-(4-propylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-heptyl-2-[4-(4-propylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-methyl-2-[4-(4-methoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-ethyl-2-[4-(4-methoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[4-(4-methoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-butyl-2-[4-(4-methoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-pentyl-2-[4-(4-methoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-hexyl-2-[4-(4-methoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-heptyl-2-[4-(4-methoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-methyl-2-[4-(4-allyloxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-ethyl-2-[4-(4-allyloxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[4-(4-allyloxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-butyl-2-[4-(4-allyloxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-pentyl-2-[4-(4-allyloxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-hexyl-2-[4-(4-allyloxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-heptyl-2-[4-(4-allyloxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-methyl-2-[4-[4-(3-butenyl)phenyl]ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-ethyl-2-[4-[4-(3-butenyl)phenyl]ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[4-[4-(3-butenyl)phenyl]ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-butyl-2-[4-[4-(3-butenyl)phenyl]ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-pentyl-2-[4-[4-(3-butenyl)phenyl]ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-hexyl-2-[4-[4-(3-butenyl)phenyl]ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-heptyl-2-[4-[4-(3-butenyl)phenyl]ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-methyl-2-[4-(4-fluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-ethyl-2-[4-(4-fluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[4-(4-fluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-butyl-2-[4-(4-fluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-pentyl-2-[4-(4-fluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-hexyl-2-[4-(4-fluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-heptyl-2-[4-(4-fluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-methyl-2-[4-(3,4-difluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-ethyl-2-[4-(3,4-difluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[4-(3,4-difluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-butyl-2-[4-(3,4-difluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-pentyl-2-[4-(3,4-difluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-hexyl-2-[4-(3,4-difluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-heptyl-2-[4-(3,4-difluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-methyl-2-[4-(3,4,5-trifluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-ethyl-2-[4-(3,4,5-trifluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[4-(3,4,5-trifluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-butyl-2-[4-(3,4,5-trifluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-pentyl-2-[4-(3,4,5-trifluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-hexyl-2-[4-(3,4,5-trifluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-heptyl-2-[4-(3,4,5-trifluorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-methyl-2-[4-(4-trifluoromethoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-ethyl-2-[4-(4-trifluoromethoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[4-(4-trifluoromethoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-butyl-2-[4-(4-trifluoromethoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-pentyl-2-[4-(4-trifluoromethoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-hexyl-2-[4-(4-trifluoromethoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-heptyl-2-[4-(4-trifluoromethoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-methyl-2-[4-(4-trifluoromethylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-ethyl-2-[4-(4-trifluoromethylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[4-(4-trifluoromethylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-butyl-2-[4-(4-trifluoromethylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-pentyl-2-[4-(4-trifluoromethylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-hexyl-2-[4-(4-trifluoromethylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-heptyl-2-[4-(4-trifluoromethylphenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-methyl-2-[4-(4-chlorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-ethyl-2-[4-(4-chlorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-propyl-2-[4-(4-chlorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-butyl-2-[4-(4-chlorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-pentyl-2-[4-(4-chlorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-hexyl-2-[4-(4-chlorophenyl)ethynylphenyl]-trans-decahydronaphthalene,-   trans-6-heptyl-2-[4-(4-chlorophenyl)ethynylphenyl]-trans-decahydronaphthalene.

Example 26 Synthesis oftrans-6-propyl-2-[2-[4-(4-cyano-3,5-difluorophenyl)phenyl]ethyl]-trans-decahydronaphthalene

(26-a) Synthesis oftrans-6-propyl-2-(2-oxoethyl)-trans-decahydronaphthalene

Reaction of 10 g oftrans-6-propyl-trans-decahydronaphthalene-2-carbaldehyde, which wasobtained in (12-a), with a Wittig reagent which is similar to that usedin (12-a) was carried out to obtain 9 g of white solidtrans-6-propyl-2-(2-oxoethyl)-trans-decahydronaphthalene.

(26-b) Synthesis oftrans-6-propyl-2-(2-phenylethyl)-trans-decahydronaphthalene

Reaction of 9 g oftrans-6-propyl-2-(2-oxoethyl)-trans-decahydronaphthalene, which wasobtained in (26-a), with a Grignard reagent similar to that used inExample 2 was carried out to obtain 11 g of white solidtrans-6-propyl-2-(2-phenylethyl)-trans-decahydronaphthalene.

(26-c) Synthesis oftrans-6-propyl-2-[2-(4-iodophenyl)ethyl]-trans-decahydronaphthalene

11 g of trans-6-propyl-2-(2-phenylethyl)-trans-decahydronaphthalene,which was obtained in (26-b), was iodized in a manner similar to that in(1-a) to obtain 13 g of pale yellow solidtrans-6-propyl-2-[2-(4-iodophenyl)ethyl]-trans-decahydronaphthalene.

(26-d) Synthesis oftrans-6-propyl-2-[2-[4-(3,5-difluorophenyl)phenyl]ethyl]-trans-decahydronaphthalene

Coupling reaction of 13 g oftrans-6-propyl-2-[2-(4-iodophenyl)ethyl]-trans-decahydronaphthalene,which was obtained in (26-c), was carried out in a manner similar tothat in (1-b) to obtain 7 g of white solidtrans-6-propyl-2-[2-[4-(3,5-difluorophenyl)phenyl]ethyl]-trans-decahydronaphthalene.

(26-e) Synthesis oftrans-6-propyl-2-[2-[4-(4-cyano-3,5-difluorophenyl)phenyl]ethyl]-trans-decahydronaphthalene

20 ml of a 1.5 M hexane solution of n-butyl lithium was added dropwiseto a 35 ml THF solution of 7 g oftrans-6-propyl-2-[2-[4-(3,5-difluorophenyl)phenyl]ethyl]-trans-decahydronaphthalene,which was obtained in (26-d), while cooling the solution to −78° C.After stirring for 10 minutes, carbon dioxide was injected into themixture until saturation. After the mixture was left to stand until thetemperature reached room temperature, 10% hydrochloric acid was added.The organic phase was extracted using ethyl acetate, rinsed with water,and dried on anhydrous magnesium sulfate. Then, the solvent wasevaporated. The pale yellow solid substance obtained was suspended in 60ml of 1,2-dichloroethane. 2 g of thionyl chloride, 0.1 ml of pyridine,and 1 ml of DMF were added to the suspension, and the mixture wasstirred for 1 hour at room temperature. The solvent was evaporated, andthe yellow oily substance obtained was dissolved in 150 ml ofdichloromethane. Ammonia gas was injected into the solution whilecooling the solution to 10° C. or lower until saturation. After stirringfor 1 hour at room temperature, the solvent was evaporated. Theyellowish brown solid substance obtained was suspended in 50 ml of DMF.2 ml of phosphorus oxychloride was added to the suspension while coolingthe suspension to 10° C. or lower, and the mixture was stirred for 3hour at room temperature. Water was added to the mixture. The organicphase was extracted using toluene, rinsed with a saturated salinesolution, and dried on anhydrous sodium sulfate. Then, the solvent wasevaporated. The residue was purified by silica gel column chromatography(hexane), and recrystallized from ethanol to obtain 1 g of white solidtrans-6-propyl-2-[2-[4-(4-cyano-3,5-difluorophenyl)phenyl]ethyl]-trans-decahydronaphthalene.

Example 27 Synthesis oftrans-6-[4-(3-butenyl)phenyl]-trans-2-vinyldecahydronaphthalene

Trans-6-(4-methoxyphenyl)-trans-2-vinyldecahydronaphthalene obtained ina manner similar to that in Example 1 was dissolved in glacial aceticacid. A 47% aqueous solution of hydrobromic acid was added to thesolution, and the mixture was heated for 20 hours under refluxing. Themixture was cooled to room temperature, and water was added to themixture. Extraction was carried out using toluene, and the organic phasewas rinsed with water and then dried on anhydrous sodium sulfate. Then,the solvent was evaporated. The oily substance obtained, which wastrans-6-(4-hydroxyphenyl)-trans-2-vinyldecahydronaphthalene, wasdissolved in methylene chloride. Trifluoromethanesulfonic anhydride wasadded dropwise to the solution while cooling the mixture at 10° C. orlower. Subsequently, pyridine was added dropwise, and the mixture wasstirred for 1 hour. Water was added, and the mixture was left to standuntil the temperature reached room temperature. Then, extraction wascarried out using ethyl acetate, and the organic phase was rinsed withwater and then dried on anhydrous sodium sulfate. Then, the solvent wasevaporated. The oily substance obtained, which wastrifluoromethanesulfonate, was dissolved in THF.Dibromobis(diphenylphosphinoethane)nickel(II) and triphenylphosphinewere added to the solution. A Grignard reagent prepared from 3-butenylbromide (1-bromo-3-butene) was added dropwise to the mixture, and themixture was heated for 16 hours under refluxing. The mixture was left tostand until the temperature reached room temperature. Then, 10%hydrochloric acid was added to the mixture, and the organic phase wasextracted using ethyl acetate, rinsed with water, and dried on anhydroussodium sulfate. After the solvent was evaporated, the residue waspurified by silica gel column chromatography (hexane) and recrystallized(ethanol) to obtain white solidtrans-6-[4-(3-butenyl)phenyl]-trans-2-vinyldecahydronaphthalene.

The following compounds were prepared in the same manner as mentionedabove:

-   trans-6-[4-(3-butenyl)phenyl]-trans-2-vinyldecahydronaphthalene,-   trans-6-(4-methylphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(4-ethylphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(4-propylphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3-fluoro-4-methylphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(4-ethyl-3-fluorophenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3-fluoro-4-propylphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-[4-(3-butenyl)-3-fluorophenyl]-trans-2-vinyldecahydronaphthalene,-   trans-6-(3,5-difluoro-4-methylphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3,5-difluoro-4-ethylphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(3,5-difluoro-4-propylphenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-[3,5-difluoro-4-(3-butenyl)phenyl]-trans-2-vinyldecahydronaphthalene,-   trans-6-(4-methylphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(4-ethylphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(4-propylphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-[4-(3-butenyl)phenyl]-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-methylphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(4-ethyl-3-fluorophenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-propylphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-[4-(3-butenyl)-3-fluorophenyl]-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-methylphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-ethylphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-propylphenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-[3,5-difluoro-4-(3-butenyl)phenyl]-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(4-methylphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(4-ethylphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(4-propylphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-[4-(3-butenyl)phenyl]-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-methylphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(4-ethyl-3-fluorophenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(3-fluoro-4-propylphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-[4-(3-butenyl)-3-fluorophenyl]-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-methylphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-ethylphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(3,5-difluoro-4-propylphenyl)-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-[3,5-difluoro-4-(3-butenyl)phenyl]-trans-2-(3-butenyl)decahydronaphthalene,-   trans-6-(4-cyanophenyl)-trans-2-vinyldecahydronaphthalene,-   trans-6-(4-cyanophenyl)-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-(4-cyanophenyl)-trans-2-(3-butenyl)decahydronaphthalene.

Example 28 Synthesis oftrans-6-[4-(2-propenyloxy)phenyl]-trans-2-vinyldecahydronaphthalene

A THF solution oftrans-6-(4-hydroxyphenyl)-trans-2-vinyldecahydronaphthalene obtained bythe method disclosed in Example 7 was added dropwise to a suspension ofsodium hydroxide in THF, the suspension being cooled to 10° C. or lower.After stirring for 30 minutes at room temperature, a THF solution of2-propenyl bromide (1-bromo-2-propene) was added dropwise, and themixture was heated for 1 hour under refluxing. The mixture was left tostand until the temperature reached room temperature, and extraction wascarried out using toluene. The organic phase was rinsed with a saturatedsaline solution and then dried on anhydrous sodium sulfate. After thesolvent was evaporated, the residue was purified by silica gel columnchromatography (hexane) and recrystallized (ethanol) to obtain whitesolidtrans-6-[4-(2-propenyloxy)phenyl]-trans-2-vinyldecahydronaphthalene.

The following compounds were prepared in the same manner as mentionedabove:

-   trans-6-[4-(trans-2-butenyloxy)phenyl]-trans-2-vinyldecahydronaphthalene,-   trans-6-[3-fluoro-4-(2-propenyloxy)phenyl]-trans-2-vinyldecahydronaphthalene,-   trans-6-[4-(trans-2-butenyloxy)-3-fluorophenyl]-trans-2-vinyldecahydronaphthalene,-   trans-6-[3,5-difluoro-4-(2-propenyloxy)phenyl]-trans-2-vinyldecahydronaphthalene.,-   trans-6-[3,5-difluoro-4-(trans-2-butenyloxy)phenyl]-trans-2-vinyldecahydronaphthalene,-   trans-6-[4-(2-propenyloxy)phenyl]-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-[4-(trans-2-butenyloxy)phenyl]-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-[3-fluoro-4-(2-propenyloxy)phenyl]-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-[4-(trans-2-butenyloxy)-3-fluorophenyl]-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-[3,5-difluoro-4-(2-propenyloxy)phenyl]-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-[3,5-difluoro-4-(trans-2-butenyloxy)phenyl]-trans-2-(1-propenyl)decahydronaphthalene,-   trans-6-[4-(2-propenyloxy)phenyl]-trans-2-(1-butenyl)decahydronaphthalene,-   trans-6-[4-(trans-2-butenyloxy)phenyl]-trans-2-(1-butenyl)decahydronaphthalene,-   trans-6-[3-fluoro-4-(2-propenyloxy)phenyl]-trans-2-(1-butenyl)decahydronaphthalene,-   trans-6-[4-(trans-2-butenyloxy)-3-fluorophenyl]-trans-2-(1-butenyl)decahydronaphthalene,-   trans-6-[3,5-difluoro-4-(2-propenyloxy)phenyl]-trans-2-(1-butenyl)decahydronaphthalene,-   trans-6-[3,5-difluoro-4-(trans-2-butenyloxy)phenyl]-trans-2-(1-butenyl)decahydronaphthalene.

Example 29 Synthesis oftrans-2-[3-fluoro-4-(2-propenyloxycarbonyl)phenyl]-trans-6-vinyldecahydronaphthalene

Trans-2-(4-carboxy-3-fluorophenyl)-trans-6-vinyldecahydronaphthaleneobtained in a manner similar to that in Example 6,dicyclohexylcarbodiimide, and N,N-dimethyl-4-aminopyridine weredissolved in methylene chloride. To this solution, a methylene chloridesolution of 2-propenol was added dropwise. After the mixture was stirredfor 20 hours at room temperature, the mixture was filtered, and solventwas evaporated. Thereafter, the residue was purified by silica gelcolumn chromatography (hexane) and recrystallized (ethanol) to obtainwhite solidtrans-2-[3-fluoro-4-(2-propenyloxycarbonyl)phenyl]-trans-6-vinyldecahydronaphthalene

Example 30 Synthesis of2-[6-(3-butenyl)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene(I-26)

(30-a) Synthesis of2-(6-methoxynaphthalen-2-yl)-trans-6-propyl-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene

In a manner similar to that in (1-a), reaction of 24 g of6-propyldecahydro-2-naphthalenone with a Grignard reagent prepared from6-methoxy-2-bromonaphthalene and dehydration were carried out to obtain32 g of pale yellow liquid2-(6-methoxynaphthalen-2-yl)-trans-6-propyl-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene.

(30-b) Synthesis of2-(6-methoxynaphthalen-2-yl)-trans-6-propyl-trans-decahydronaphthalene

In a manner similar to that in (1-e), catalytic hydrogenation reductionand isomerization of 32 g of2-(6-methoxynaphthalen-2-yl)-trans-6-propyl-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene,which was obtained in (30-a), were carried out to obtain 30 g of2-(6-methoxynaphthalen-2-yl)-trans-6-propyl-trans-decahydronaphthaleneas a pale yellow oily substance.

(30-c) Synthesis of6-(trans-6-propyl-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl)-2-naphthol

30 g oftrans-2-propyl-trans-6-(3-fluoro-4-methoxyphenyl)-trans-decahydronaphthalene,which was obtained in (30-b), was dissolved in a mixture of 150 ml ofglacial acetic acid and 150 ml of 48% hydrobromic acid, and the solutionwas heated for 8 hours under refluxing. The solution was cooled to roomtemperature. Water and ethyl acetate were added to the solution. Afterthe organic phase was separated, the organic phase was rinsed withwater, a saturated aqueous solution of sodium hydrogencarbonate, water,and a saturated saline solution, in sequence, and dried on anhydroussodium sulfate. The solvent was evaporated to obtain 24 g yellowcrystals of6-(trans-6-propyl-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl)-2-naphthol.

(30-d) Synthesis of2-(6-trifluoromethanesulfonyloxynaphthalen-2-yl)-trans-6-propyl-trans-decahydronaphthalene

A 120 ml dichloromethane solution of 25 g of trifluoromethanesulfonicanhydride was added dropwise to a 100 ml dichloromethane solution of 24g yellow crystals of6-(trans-6-propyl-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl)-2-naphthol,which were obtained in (30-c), while the solution was cooled at 0°.Subsequently, a 70 ml dichloromethane solution of 14 g of pyridine wasadded dropwise. After the mixture was stirred for 1 hour at roomtemperature, 10% hydrochloric acid was added, and the organic phase wasseparated and rinsed with water, a saturated aqueous solution of sodiumhydrogencarbonate, water, and a saturated saline solution, in sequence,and dried on anhydrous sodium sulfate. The solvent was evaporated, andthe residue was purified by silica gel column chromatography (hexane) toobtain 25 g of white solid2-(6-trifluoromethanesulfonyloxynaphthalen-2-yl)-trans-6-propyl-trans-decahydronaphthalene.

(30-e) Synthesis of2-[6-(3-butenyl)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene

A Grignard reagent prepared from 1.5 g of metal magnesium and 9 g of4-bromo-1-butene was added dropwise to a 130 ml THF solution of 25 g of2-(6-trifluoromethanesulfonyloxynaphthalen-2-yl)-trans-6-propyl-trans-decahydronaphthalene,which was obtained in (30-d), and 0.8 g ofdichlorobis(diphenylphosphinoethane)nickel(II), the solution beingcooled to 10° C. or lower. The temperature was reduced to roomtemperature, and the mixture was stirred for 6 hours. After 10%hydrochloric acid was added, the organic phase was separated, rinsedwith water and a saturated saline solution, in sequence, and dried onanhydrous magnesium sulfate. The solvent was evaporated, and the residuewas purified by silica gel column chromatography (hexane) andrecrystallized from ethanol to obtain 3 g white crystals of2-[6-(3-butenyl)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene

The following compounds were prepared in the same manner as mentionedabove:

-   2-[6-(3-butenyl)naphthalen-2-yl)-6-methyl-trans-decahydronaphthalene,-   2-[6-(3-butenyl)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[6-(3-butenyl)naphthalen-2-yl]-6-butyl-trans-decahydronaphthalene,-   2-[6-(3-butenyl)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[6-(3-butenyl)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[6-(3-butenyl)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[6-(trans-3-pentenyl)naphthalen-2-yl)-6-methyl-trans-decahydronaphthalene,-   2-[6-(trans-3-pentenyl)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[6-(trans-3-pentenyl)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene,-   2-[6-(trans-3-pentenyl)naphthalen-2-yl]-6-butyl-trans-decahydronaphthalene,-   2-[6-(trans-3-pentenyl)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[6-(trans-3-pentenyl)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[6-(trans-3-pentenyl)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(6-methoxynaphthalen-2-yl)-6-methyl-trans-decahydronaphthalene,-   2-(6-methoxynaphthalen-2-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(6-methoxynaphthalen-2-yl)-6-propyl-trans-decahydronaphthalene,-   2-(6-methoxynaphthalen-2-yl)-6-butyl-trans-decahydronaphthalene,-   2-(6-methoxynaphthalen-2-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(6-methoxynaphthalen-2-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(6-methoxynaphthalen-2-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[6-(2-propenyloxy)naphthalen-2-yl]-6-methyl-trans-decahydronaphthalene,-   2-[6-(2-propenyloxy)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[6-(2-propenyloxy)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene,-   2-[6-(2-propenyloxy)naphthalen-2-yl]-6-butyl-trans-decahydronaphthalene,-   2-[6-(2-propenyloxy)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[6-(2-propenyloxy)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[6-(2-propenyloxy)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[6-(trans-2-butenyloxy)naphthalen-2-yl]-6-methyl-trans-decahydronaphthalene,-   2-[6-(trans-2-butenyloxy)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[6-(trans-2-butenyloxy)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene,-   2-[6-(trans-2-butenyloxy)naphthalen-2-yl]-6-butyl-trans-decahydronaphthalene,-   2-[6-(trans-2-butenyloxy)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[6-(trans-2-butenyloxy)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[6-(trans-2-butenyloxy)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(1-fluoro-2-methoxynaphthalen-6-yl)-6-methyl-trans-decahydronaphthalene,-   2-(1-fluoro-2-methoxynaphthalen-6-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(1-fluoro-2-methoxynaphthalen-6-yl)-6-propyl-trans-decahydronaphthalene,-   2-(1-fluoro-2-methoxynaphthalen-6-yl)-6-butyl-trans-decahydronaphthalene,-   2-(1-fluoro-2-methoxynaphthalen-6-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(1-fluoro-2-methoxynaphthalen-6-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(1-fluoro-2-methoxynaphthalen-6-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(3-fluoro-2-methoxynaphthalen-6-yl)-6-methyl-trans-decahydronaphthalene,-   2-(3-fluoro-2-methoxynaphthalen-6-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(3-fluoro-2-methoxynaphthalen-6-yl)-6-propyl-trans-decahydronaphthalene,-   2-(3-fluoro-2-methoxynaphthalen-6-yl)-6-butyl-trans-decahydronaphthalene,-   2-(3-fluoro-2-methoxynaphthalen-6-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(3-fluoro-2-methoxynaphthalen-6-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(3-fluoro-2-methoxynaphthalen-6-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-(3-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-(3-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(1,3-difluoro-2-methoxynaphthalen-6-yl)-6-methyl-trans-decahydronaphthalene,-   2-(1,3-difluoro-2-methoxynaphthalen-6-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(1,3-difluoro-2-methoxynaphthalen-6-yl)-6-propyl-trans-decahydronaphthalene,-   2-(1,3-difluoro-2-methoxynaphthalen-6-yl)-6-butyl-trans-decahydronaphthalene,-   2-(1,3-difluoro-2-methoxynaphthalen-6-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(1,3-difluoro-2-methoxynaphthalen-6-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(1,3-difluoro-2-methoxynaphthalen-6-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(2-propenyloxy)naphthalen-6-yl)-6-pentyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl)-6-ethyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,3-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(3-butenyl)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(3-butenyl)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(3-butenyl)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(3-butenyl)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(3-butenyl)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(3-butenyl)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(3-butenyl)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-3-pentenyl)naphthalen-7-yl)-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-methyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-propyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-butyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(1,2-difluoro-3-methoxynaphthalen-7-yl)-6-methyl-trans-decahydronaphthalene,-   2-(1,2-difluoro-3-methoxynaphthalen-7-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(1,2-difluoro-3-methoxynaphthalen-7-yl)-6-propyl-trans-decahydronaphthalene,-   2-(1,2-difluoro-3-methoxynaphthalen-7-yl)-6-butyl-trans-decahydronaphthalene,-   2-(1,2-difluoro-3-methoxynaphthalen-7-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(1,2-difluoro-3-methoxynaphthalen-7-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(1,2-difluoro-3-methoxynaphthalen-7-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-(1,2-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-(1,2-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-7-(3-butenyl)naphthalen-3-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-7-(3-butenyl)naphthalen-3-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-7-(3-butenyl)naphthalen-3-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-7-(3-butenyl)naphthalen-3-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-7-(3-butenyl)naphthalen-3-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-7-(3-butenyl)naphthalen-3-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-7-(3-butenyl)naphthalen-3-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-7-(trans-3-pentenyl)naphthalen-3-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-7-(trans-3-pentenyl)naphthalen-3-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-7-(trans-3-pentenyl)naphthalen-3-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-7-(trans-3-pentenyl)naphthalen-3-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-7-(trans-3-pentenyl)naphthalen-3-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-7-(trans-3-pentenyl)naphthalen-3-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-7-(trans-3-pentenyl)naphthalen-3-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-methyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-propyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-butyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl)-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-methyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-propyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-butyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(1-fluoro-3-methoxynaphthalen-7-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(3-butenyl)naphthalen-2-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(3-butenyl)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-6-(3-butenyl)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(3-butenyl)naphthalen-2-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(3-butenyl)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(3-butenyl)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(3-butenyl)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(trans-3-pentenyl)naphthalen-2-yl)-6-methyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-6-methoxynaphthalen-2-yl)-6-methyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-6-methoxynaphthalen-2-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-6-methoxynaphthalen-2-yl)-6-propyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-6-methoxynaphthalen-2-yl)-6-butyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-6-methoxynaphthalen-2-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-6-methoxynaphthalen-2-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-6-methoxynaphthalen-2-yl)-6-heptyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(2-propenyloxy)naphthalen-2-yl)-6-butyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-(1,6-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(1,6-difluoro-3-methoxynaphthalen-7-yl)-6-methyl-trans-decahydronaphthalene,-   2-(1,6-difluoro-3-methoxynaphthalen-7-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(1,6-difluoro-3-methoxynaphthalen-7-yl)-6-propyl-trans-decahydronaphthalene,-   2-(1,6-difluoro-3-methoxynaphthalen-7-yl)-6-butyl-trans-decahydronaphthalene,-   2-(1,6-difluoro-3-methoxynaphthalen-7-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(1,6-difluoro-3-methoxynaphthalen-7-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(1,6-difluoro-3-methoxynaphthalen-7-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl)-6-pentyl-trans-decahydronaphthalene,-   2-[1,6-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-(1,6-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(3-butenyl)naphthalen-2-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(3-butenyl)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(3-butenyl)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(3-butenyl)naphthalen-2-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(3-butenyl)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(3-butenyl)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(3-butenyl)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(1,3,8-trifluoro-6-methoxynaphthalen-2-yl)-6-methyl-trans-decahydronaphthalene,-   2-(1,3,8-trifluoro-6-methoxynaphthalen-2-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(1,3,8-trifluoro-6-methoxynaphthalen-2-yl)-6-propyl-trans-decahydronaphthalene,-   2-(1,3,8-trifluoro-6-methoxynaphthalen-2-yl)-6-butyl-trans-decahydronaphthalene,-   2-(1,3,8-trifluoro-6-methoxynaphthalen-2-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(1,3,8-trifluoro-6-methoxynaphthalen-2-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(1,3,8-trifluoro-6-methoxynaphthalen-2-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,3,8-trifluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(3-fluoro-2-methoxynaphthalen-6-yl)-6-methyl-trans-decahydronaphthalene,-   2-(3-fluoro-2-methoxynaphthalen-6-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(3-fluoro-2-methoxynaphthalen-6-yl)-6-propyl-trans-decahydronaphthalene,-   2-(3-fluoro-2-methoxynaphthalen-6-yl)-6-butyl-trans-decahydronaphthalene,-   2-(3-fluoro-2-methoxynaphthalen-6-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(3-fluoro-2-methoxynaphthalen-6-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(3-fluoro-2-methoxynaphthalen-6-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[3-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(3-butenyl)naphthalen-2-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(3-butenyl)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(3-butenyl)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(3-butenyl)naphthalen-2-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(3-butenyl)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(3-butenyl)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(3-butenyl)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(trans-3-pentenyl)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(1,7-difluoro-6-methoxynaphthalen-2-yl)-6-methyl-trans-decahydronaphthalene,-   2-(1,7-difluoro-6-methoxynaphthalen-2-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(1,7-difluoro-6-methoxynaphthalen-2-yl)-6-propyl-trans-decahydronaphthalene,-   2-(1,7-difluoro-6-methoxynaphthalen-2-yl)-6-butyl-trans-decahydronaphthalene,-   2-(1,7-difluoro-6-methoxynaphthalen-2-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(1,7-difluoro-6-methoxynaphthalen-2-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(1,7-difluoro-6-methoxynaphthalen-2-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(2-propenyloxy)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,7-di    fluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-6-(trans-2-butenyloxy)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(3-butenyl)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(1,2-difluoro-3-methoxynaphthalen-7-yl)-6-methyl-trans-decahydronaphthalene,-   2-(1,2-difluoro-3-methoxynaphthalen-7-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(1,2-difluoro-3-methoxynaphthalen-7-yl)-6-propyl-trans-decahydronaphthalene,-   2-(1,2-difluoro-3-methoxynaphthalen-7-yl)-6-butyl-trans-decahydronaphthalene,-   2-(1,2-difluoro-3-methoxynaphthalen-7-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(1,2-difluoro-3-methoxynaphthalen-7-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(1,2-difluoro-3-methoxynaphthalen-7-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,2-difluoro-3-(trans-2-butenyloxy)naphthalen-7-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(3-butenyl)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-3-(3-butenyl)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(3-butenyl)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(3-butenyl)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(3-butenyl)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(3-butenyl)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(3-butenyl)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(trans-3-pentenyl)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-3-methoxynaphthalen-7-yl)-6-methyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-3-methoxynaphthalen-7-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-3-methoxynaphthalen-7-yl)-6-propyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-3-methoxynaphthalen-7-yl)-6-butyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-3-methoxynaphthalen-7-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-3-methoxynaphthalen-7-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-3-methoxynaphthalen-7-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(2-propenyloxy)naphthalen-7-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(trans-2-butenyloxy)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(trans-2-butenyloxy)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(trans-2-butenyloxy)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(trans-2-butenyloxy)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(trans-2-butenyloxy)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(trans-2-butenyloxy)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-3-(trans-2-butenyloxy)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(3-butenyl)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(1-fluoro-2-methoxynaphthalen-6-yl)-6-methyl-trans-decahydronaphthalene,-   2-(1-fluoro-2-methoxynaphthalen-6-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(1-fluoro-2-methoxynaphthalen-6-yl)-6-propyl-trans-decahydronaphthalene,-   2-(1-fluoro-2-methoxynaphthalen-6-yl)-6-butyl-trans-decahydronaphthalene,-   2-(1-fluoro-2-methoxynaphthalen-6-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(1-fluoro-2-methoxynaphthalen-6-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(1-fluoro-2-methoxynaphthalen-6-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1-fluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(1,7-difluoro-2-methoxynaphthalen-6-yl)-6-methyl-trans-decahydronaphthalene,-   2-(1,7-difluoro-2-methoxynaphthalen-6-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(1,7-difluoro-2-methoxynaphthalen-6-yl)-6-propyl-trans-decahydronaphthalene,-   2-(1,7-difluoro-2-methoxynaphthalen-6-yl)-6-butyl-trans-decahydronaphthalene,-   2-(1,7-difluoro-2-methoxynaphthalen-6-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(1,7-difluoro-2-methoxynaphthalen-6-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(1,7-difluoro-2-methoxynaphthalen-6-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,7-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(3-butenyl)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(trans-3-pentenyl)naphthalen-6-yl)-6-heptyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-2-methoxynaphthalen-6-yl)-6-methyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-2-methoxynaphthalen-6-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-2-methoxynaphthalen-6-yl)-6-propyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-2-methoxynaphthalen-6-yl)-6-butyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-2-methoxynaphthalen-6-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-2-methoxynaphthalen-6-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-2-methoxynaphthalen-6-yl)-6-heptyl-trans-decahydronaphthalene,-   2-(1,8-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(2-propenyloxy)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,8-difluoro-2-(trans-2-butenyloxy)naphthalen-6-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(3-butenyl)naphthalen-3-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(3-butenyl)naphthalen-3-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(3-butenyl)naphthalen-3-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(3-butenyl)naphthalen-3-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(3-butenyl)naphthalen-3-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(3-butenyl)naphthalen-3-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(3-butenyl)naphthalen-3-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(trans-3-pentenyl)naphthalen-3-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(trans-3-pentenyl)naphthalen-3-yl)-6-ethyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(trans-3-pentenyl)naphthalen-3-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(trans-3-pentenyl)naphthalen-3-yl)-6-butyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(trans-3-pentenyl)naphthalen-3-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(trans-3-pentenyl)naphthalen-3-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(trans-3-pentenyl)naphthalen-3-yl]-6-heptyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-7-methoxynaphthalen-3-yl)-6-methyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-7-methoxynaphthalen-3-yl)-6-ethyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-7-methoxynaphthalen-3-yl)-6-propyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-7-methoxynaphthalen-3-yl)-6-butyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-7-methoxynaphthalen-3-yl)-6-pentyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-7-methoxynaphthalen-3-yl)-6-hexyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-7-methoxynaphthalen-3-yl)-6-heptyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(2-propenyloxy)naphthalen-3-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(2-propenyloxy)naphthalen-3-yl]-6-ethyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(2-propenyloxy)naphthalen-3-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(2-propenyloxy)naphthalen-3-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(2-propenyloxy)naphthalen-3-yl]-6-pentyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-7-(2-propenyloxy)naphthalen-3-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(2-propenyloxy)naphthalen-3-yl]-6-heptyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(trans-2-butenyloxy)naphthalen-3-yl]-6-methyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(trans-2-butenyloxy)naphthalen-3-yl]-6-ethyl-trans-decahydronaphthalene,-   2-(1,2,8-trifluoro-7-(trans-2-butenyloxy)naphthalen-3-yl]-6-propyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(trans-2-butenyloxy)naphthalen-3-yl]-6-butyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(trans-2-butenyloxy)naphthalen-3-yl]-6-pentyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(trans-2-butenyloxy)naphthalen-3-yl]-6-hexyl-trans-decahydronaphthalene,-   2-[1,2,8-trifluoro-7-(trans-2-butenyloxy)naphthalen-3-yl]-6-heptyl-trans-decahydronaphthalene.

Example 31 Synthesis of6-(6-propyltetrahydronaphthalen-2-yl)-2-vinyl-trans-decahydronaphthalene(I-28)

(31-a) Synthesis of4-(3-propyridenebicyclo[4.4.0]decan-8-yl)cyclohexanone ethyleneacetal

Reaction of 10 g of4-(6-oxo-trans-decahydronaphthalen-2-yl)cyclohexanone ethyleneacetalwith a Wittig reagent was carried out in a manner similar to that in(6-e) to obtain 9 g of white solid4-(3-propyridenebicyclo[4.4.0]decan-8-yl)cyclohexanone ethyleneacetal.

(31-b) Synthesis of4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)cyclohexanoneethyleneacetal

In a manner similar to that in (1-e), catalytic hydrogenation reductionof 9 g of 4-(3-propyridenebicyclo[4.4.0]decan-8-yl)cyclohexanoneethyleneacetal, which was obtained in (31-a), was carried out to obtain8 g of pale yellow solid4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)cyclohexanoneethyleneacetal.

(31-c) Synthesis of4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)cyclohexanone

In a manner similar to that in (1-c), deacetalization of 8 g of4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)cyclohexanoneethyleneacetal, which was obtained in (31-b), was carried out to obtain6 g of pale yellow solid4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)cyclohexanone.

(31-d) Synthesis of6-(trans-6-propyl-trans-decahydronaphthalen-2-yl)-4,4a,5,6,7,8-hexahydro-3H-2-naphthalenone

6 g of 4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)cyclohexanone,which was obtained in (31-c), was dissolved in 30 ml of toluene, and 15ml of pyrrolidine was added to the solution. The mixture was heated for4 hours under refluxing using an apparatus equipped with a waterseparator until-evaporation of water stopped. Pyrrolidine and toluenewere evaporated while the heating was maintained, then the temperaturewas reduced to room temperature, and 40 ml of toluene was added to themixture. While cooling the mixture to 20° C. or lower, 8 ml of methylvinyl ketone was added dropwise over a period of 5 minutes. After thedropwise addition, the mixture was heated for 2 hours under refluxing,and then the mixture was left to cool to room temperature. An aqueoussolution in which 3 g of sodium acetate, 10 ml of glacial acetic acid,and 10 ml of water were mixed was added. After The mixture was heatedfor 2 hours under refluxing, the mixture was left to cool to roomtemperature. The organic phase was separated and rinsed with water, andthe solvent was evaporated. 8 g of the oily substance obtained wasdissolved in 40 ml of THF, and 30 ml of 3 M hydrochloric acid was addedto the solution. After heating the mixture for 5 hours under refluxing,the temperature was reduced to room temperature, and the organic phasewas separated, rinsed with a saturated saline solution, and dried onanhydrous magnesium sulfate. The solvent was evaporated to obtain 8 g ofbrown solid6-(trans-6-propyl-trans-decahydronaphthalen-2-yl)-4,4a,5,6,7,8-hexahydro-3H-2-naphthalenone.

(31-e) Synthesis of6-(trans-6-propyl-trans-decahydronaphthalen-2-yl)-trans-decahydro-2-naphthalenone

A 40 ml THF solution of 8 g of6-(trans-6-propyl-trans-decahydronaphthalen-2-yl)-4,4a,5,6,7,8-hexahydro-3H-2-naphthalenone,which was obtained in (31-d), and 20 ml of t-butanol was added dropwiseto a solution of 2 g of metal lithium in 100 ml of liquid ammonia whilemaintaining the inner temperature between −30° C. and −40° C. After thedropwise addition, stirring was continued for 30 minutes. After solidammonium chloride was added in small amounts to the mixture to oxidizelithium, the temperature was raised to room temperature, and ammonia wasevaporated. Water was added, and extraction was carried out usingtoluene. The organic phase was rinsed with a saturated saline solutionand dried on anhydrous magnesium sulfate, and the solvent wasevaporated. The residue was purified by silica gel column chromatography(toluene) and recrystallized from a hexane solution to obtain 4 g ofpale yellow liquid6-(trans-6-propyl-trans-decahydronaphthalen-2-yl)-trans-decahydro-2-naphthalenone

(31-f) Synthesis of6-(6-propyl-trans-decahydronaphthalen-2-yl)-trans-decahydronaphthalene-2-carbaldehyde

In a manner similar to that of (6-a), reaction of 6 g of6-(6-propyl-trans-decahydronaphthalen-2-yl)-trans-decahydro-2-naphthalenone,which was obtained in (31-f), with a Wittig reagent was carried out toobtain 4 g of pale yellow solid6-(6-propyl-trans-decahydronaphthalen-2-yl)-trans-decahydronaphthalene-2-carbaldehyde.

(31-g) Synthesis of6-(6-propyl-trans-decahydronaphthalen-2-yl)-2-vinyl-trans-decahydronaphthalene

In a manner similar to that of (6-e), reaction of 4 g of6-(6-propyl-trans-decahydronaphthalen-2-yl)-trans-decahydronaphthalene-2-carbaldehyde,which was obtained in (31-f), with a Wittig reagent was carried out toobtain 2 g of white solid6-(6-propyl-trans-decahydronaphthalen-2-yl)-2-vinyl-trans-decahydronaphthalene.

The following compounds were prepared in the same manner as mentionedabove:

-   6-(6-methyltetrahydronaphthalen-2-yl)-2-methyl-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-propyl-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-butyl-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-methoxy-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-ethoxy-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-propyloxy-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-butyloxy-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-pentyloxy-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-hexyloxy-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-vinyl-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-(trans-1-propenyl)-trans-decahydronaphthalene,-   6-[6-methyltetrahydronaphthalen-2-yl]-2-(3-butenyl)-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-(6-methyltetrahydronaphthalen-2-yl)-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-ethyl-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-propyl-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-butyl-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-methoxy-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-ethoxy-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-propyloxy-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-butyloxy-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-pentyloxy-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-hexyloxy-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-vinyl-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-(trans-1-propenyl)-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-(3-butenyl)-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-(6-ethyltetrahydronaphthalen-2-yl)-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-propyl-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-butyl-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-methoxy-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-ethoxy-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-propyloxy-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-butyloxy-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-pentyloxy-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-hexyloxy-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-(trans-1-propenyl)-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-(3-butenyl)-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-(6-propyltetrahydronaphthalen-2-yl)-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-butyl-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-methoxy-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-ethoxy-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-propyloxy-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-butyloxy-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-pentyloxy-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-hexyloxy-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-vinyl-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-(trans-1-propenyl)-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-(3-butenyl)-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-(6-butyltetrahydronaphthalen-2-yl)-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-pentyl-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-methoxy-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-ethoxy-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-propyloxy-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-butyloxy-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-pentyloxy-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-hexyloxy-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-vinyl-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-(trans-1-propenyl)-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-(3-butenyl)-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-(6-pentyltetrahydronaphthalen-2-yl)-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-(6-hexyltetrahydronaphthalen-2-yl)-2-hexyl-trans-decahydronaphthalene,-   6-(6-hexyltetrahydronaphthalen-2-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(6-hexyltetrahydronaphthalen-2-yl)-2-methoxy-trans-decahydronaphthalene,-   6-(6-hexyltetrahydronaphthalen-2-yl)-2-ethoxy-trans-decahydronaphthalene,-   6-(6-hexyltetrahydronaphthalen-2-yl)-2-propyloxy-trans-decahydronaphthalene,-   6-(6-hexyltetrahydronaphthalen-2-yl)-2-butyloxy-trans-decahydronaphthalene,-   6-(6-hexyltetrahydronaphthalen-2-yl)-2-pentyloxy-trans-decahydronaphthalene,-   6-(6-hexyltetrahydronaphthalen-2-yl)-2-hexyloxy-trans-decahydronaphthalene,-   6-(6-hexyltetrahydronaphthalen-2-yl)-2-vinyl-trans-decahydronaphthalene,-   6-(6-hexyltetrahydronaphthalen-2-yl)-2-(trans-1-propenyl)-trans-decahydronaphthalene,-   6-(6-hexyltetrahydronaphthalen-2-yl)-2-(3-butenyl)-trans-decahydronaphthalene,-   6-(6-hexyltetrahydronaphthalen-2-yl)-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-(6-hexyltetrahydronaphthalen-2-yl)-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-(6-hexyltetrahydronaphthalen-2-yl)-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-(6-hexyltetrahydronaphthalen-2-yl)-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-(6-hexyltetrahydronaphthalen-2-yl)-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-(6-heptyltetrahydronaphthalen-2-yl)-2-heptyl-trans-decahydronaphthalene,-   6-(6-heptyltetrahydronaphthalen-2-yl)-2-methoxy-trans-decahydronaphthalene,-   6-(6-heptyltetrahydronaphthalen-2-yl)-2-ethoxy-trans-decahydronaphthalene,-   6-(6-heptyltetrahydronaphthalen-2-yl)-2-propyloxy-trans-decahydronaphthalene,-   6-(6-heptyltetrahydronaphthalen-2-yl)-2-butyloxy-trans-decahydronaphthalene,-   6-(6-heptyltetrahydronaphthalen-2-yl)-2-pentyloxy-trans-decahydronaphthalene,-   6-(6-heptyltetrahydronaphthalen-2-yl)-2-hexyloxy-trans-decahydronaphthalene,-   6-(6-heptyltetrahydronaphthalen-2-yl)-2-vinyl-trans-decahydronaphthalene,-   6-(6-heptyltetrahydronaphthalen-2-yl)-2-(trans-1-propenyl)-trans-decahydronaphthalene,-   6-(6-heptyltetrahydronaphthalen-2-yl)-2-(3-butenyl)-trans-decahydronaphthalene,-   6-(6-heptyltetrahydronaphthalen-2-yl)-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-(6-heptyltetrahydronaphthalen-2-yl)-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-(6-heptyltetrahydronaphthalen-2-yl)-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-(6-heptyltetrahydronaphthalen-2-yl)-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-(6-heptyltetrahydronaphthalen-2-yl)-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-(6-methoxytetrahydronaphthalen-2-yl)-2-methoxy-trans-decahydronaphthalene,-   6-(6-methoxytetrahydronaphthalen-2-yl)-2-ethoxy-trans-decahydronaphthalene,-   6-(6-methoxytetrahydronaphthalen-2-yl)-2-propyloxy-trans-decahydronaphthalene,-   6-(6-methoxytetrahydronaphthalen-2-yl)-2-butyloxy-trans-decahydronaphthalene,-   6-(6-methoxytetrahydronaphthalen-2-yl)-2-pentyloxy-trans-decahydronaphthalene,-   6-(6-methoxytetrahydronaphthalen-2-yl)-2-hexyloxy-trans-decahydronaphthalene,-   6-(6-methoxytetrahydronaphthalen-2-yl)-2-vinyl-trans-decahydronaphthalene,-   6-(6-methoxytetrahydronaphthalen-2-yl)-2-(trans-1-propenyl)-trans-decahydronaphthalene,-   6-(6-methoxytetrahydronaphthalen-2-yl)-2-(3-butenyl)-trans-decahydronaphthalene,-   6-(6-methoxytetrahydronaphthalen-2-yl)-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-(6-methoxytetrahydronaphthalen-2-yl)-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-(6-methoxytetrahydronaphthalen-2-yl)-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-(6-methoxytetrahydronaphthalen-2-yl)-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-(6-methoxytetrahydronaphthalen-2-yl)-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-(6-ethoxytetrahydronaphthalen-2-yl)-2-ethoxy-trans-decahydronaphthalene,-   6-(6-ethoxytetrahydronaphthalen-2-yl)-2-propyloxy-trans-decahydronaphthalene,-   6-(6-ethoxytetrahydronaphthalen-2-yl)-2-butyloxy-trans-decahydronaphthalene,-   6-(6-ethoxytetrahydronaphthalen-2-yl)-2-pentyloxy-trans-decahydronaphthalene,-   6-(6-ethoxytetrahydronaphthalen-2-yl)-2-hexyloxy-trans-decahydronaphthalene,-   6-(6-ethoxytetrahydronaphthalen-2-yl)-2-vinyl-trans-decahydronaphthalene,-   6-(6-ethoxytetrahydronaphthalen-2-yl)-2-(trans-1-propenyl)-trans-decahydronaphthalene,-   6-(6-ethoxytetrahydronaphthalen-2-yl)-2-(3-butenyl)-trans-decahydronaphthalene,-   6-(6-ethoxytetrahydronaphthalen-2-yl)-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-(6-ethoxytetrahydronaphthalen-2-yl)-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-(6-ethoxytetrahydronaphthalen-2-yl)-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-(6-ethoxytetrahydronaphthalen-2-yl)-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-(6-ethoxytetrahydronaphthalen-2-yl)-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-(6-propyloxytetrahydronaphthalen-2-yl)-2-propyloxy-trans-decahydronaphthalene,-   6-(6-propyloxytetrahydronaphthalen-2-yl)-2-butyloxy-trans-decahydronaphthalene,-   6-(6-propyloxytetrahydronaphthalen-2-yl)-2-pentyloxy-trans-decahydronaphthalene,-   6-(6-propyloxytetrahydronaphthalen-2-yl)-2-hexyloxy-trans-decahydronaphthalene,-   6-(6-propyloxytetrahydronaphthalen-2-yl)-2-vinyl-trans-decahydronaphthalene,-   6-(6-propyloxytetrahydronaphthalen-2-yl)-2-(trans-1-propenyl)-trans-decahydronaphthalene,-   6-(6-propyloxytetrahydronaphthalen-2-yl)-2-(3-butenyl)-trans-decahydronaphthalene,-   6-(6-propyloxytetrahydronaphthalen-2-yl)-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-(6-propyloxytetrahydronaphthalen-2-yl)-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-(6-propyloxytetrahydronaphthalen-2-yl)-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-(6-propyloxytetrahydronaphthalen-2-yl)-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-(6-propyloxytetrahydronaphthalen-2-yl)-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-(6-butyloxytetrahydronaphthalen-2-yl)-2-butyloxy-trans-decahydronaphthalene,-   6-(6-butyloxytetrahydronaphthalen-2-yl)-2-pentyloxy-trans-decahydronaphthalene,-   6-(6-butyloxytetrahydronaphthalen-2-yl)-2-hexyloxy-trans-decahydronaphthalene,-   6-(6-butyloxytetrahydronaphthalen-2-yl)-2-vinyl-trans-decahydronaphthalene,-   6-(6-butyloxytetrahydronaphthalen-2-yl)-2-(trans-1-propenyl)-trans-decahydronaphthalene,-   6-(6-butyloxytetrahydronaphthalen-2-yl)-2-(3-butenyl)-trans-decahydronaphthalene,-   6-(6-butyloxytetrahydronaphthalen-2-yl)-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-(6-butyloxytetrahydronaphthalen-2-yl)-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-(6-butyloxytetrahydronaphthalen-2-yl)-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-(6-butyloxytetrahydronaphthalen-2-yl)-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-(6-butyloxytetrahydronaphthalen-2-yl)-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-(6-pentyloxytetrahydronaphthalen-2-yl)-2-pentyloxy-trans-decahydronaphthalene,-   6-(6-pentyloxytetrahydronaphthalen-2-yl)-2-hexyloxy-trans-decahydronaphthalene,-   6-(6-pentyloxytetrahydronaphthalen-2-yl)-2-vinyl-trans-decahydronaphthalene,-   6-(6-pentyloxytetrahydronaphthalen-2-yl)-2-(trans-1-propenyl)-trans-decahydronaphthalene,-   6-(6-pentyloxytetrahydronaphthalen-2-yl)-2-(3-butenyl)-trans-decahydronaphthalene,-   6-(6-pentyloxytetrahydronaphthalen-2-yl)-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-(6-pentyloxytetrahydronaphthalen-2-yl)-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-(6-pentyloxytetrahydronaphthalen-2-yl)-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-(6-pentyloxytetrahydronaphthalen-2-yl)-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-(6-pentyloxytetrahydronaphthalen-2-yl)-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-(6-hexyloxytetrahydronaphthalen-2-yl)-2-hexyloxy-trans-decahydronaphthalene,-   6-(6-hexyloxytetrahydronaphthalen-2-yl)-2-vinyl-trans-decahydronaphthalene,-   6-(6-hexyloxytetrahydronaphthalen-2-yl)-2-(trans-1-propenyl)-trans-decahydronaphthalene,-   6-(6-hexyloxytetrahydronaphthalen-2-yl)-2-(3-butenyl)-trans-decahydronaphthalene,-   6-(6-hexyloxytetrahydronaphthalen-2-yl)-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-(6-hexyloxytetrahydronaphthalen-2-yl)-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-(6-hexyloxytetrahydronaphthalen-2-yl)-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-(6-hexyloxytetrahydronaphthalen-2-yl)-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-(6-hexyloxytetrahydronaphthalen-2-yl)-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-(6-vinyltetrahydronaphthalen-2-yl)-2-vinyl-trans-decahydronaphthalene,-   6-(6-vinyltetrahydronaphthalen-2-yl)-2-(trans-1-propenyl)-trans-decahydronaphthalene,-   6-(6-vinyltetrahydronaphthalen-2-yl)-2-(3-butenyl)-trans-decahydronaphthalene,-   6-(6-vinyltetrahydronaphthalen-2-yl)-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-(6-vinyltetrahydronaphthalen-2-yl)-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-(6-vinyltetrahydronaphthalen-2-yl)-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-(6-vinyltetrahydronaphthalen-2-yl)-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-(6-vinyltetrahydronaphthalen-2-yl)-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-[6-(trans-1-propenyl)-tetrahydronaphthalen-2-yl]-2-(trans-1-propenyl)-trans-decahydronaphthalene,-   6-[6-(trans-1-propenyl)-tetrahydronaphthalen-2-yl]-2-(3-butenyl)-trans-decahydronaphthalene,-   6-[6-(trans-1-propenyl)-tetrahydronaphthalen-2-yl]-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-[6-(trans-1-propenyl)-tetrahydronaphthalen-2-yl]-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-[6-(trans-1-propenyl)-tetrahydronaphthalen-2-yl]-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-[6-(trans-1-propenyl)-tetrahydronaphthalen-2-yl]-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-[6-(trans-1-propenyl)-tetrahydronaphthalen-2-yl]-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-[6-(3-butenyl)-tetrahydronaphthalen-2-yl]-2-(3-butenyl)-trans-decahydronaphthalene,-   6-[6-(3-butenyl)-tetrahydronaphthalen-2-yl]-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-[6-(3-butenyl)-tetrahydronaphthalen-2-yl]-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-[6-(3-butenyl)-tetrahydronaphthalen-2-yl]-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-[6-(3-butenyl)-tetrahydronaphthalen-2-yl]-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-[6-(3-butenyl)-tetrahydronaphthalen-2-yl]-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-[6-(trans-3-pentenyl)-tetrahydronaphthalen-2-yl]-2-(trans-3-pentenyl)-trans-decahydronaphthalene,-   6-[6-(trans-3-pentenyl)-tetrahydronaphthalen-2-yl]-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-[6-(trans-3-pentenyl)-tetrahydronaphthalen-2-yl]-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-[6-(trans-3-pentenyl)-tetrahydronaphthalen-2-yl]-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-[6-(trans-3-pentenyl)-tetrahydronaphthalen-2-yl]-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-[6-(2-propenyloxy)-tetrahydronaphthalen-2-yl]-2-(2-propenyloxy)-trans-decahydronaphthalene,-   6-[6-(2-propenyloxy)-tetrahydronaphthalen-2-yl]-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-[6-(2-propenyloxy)-tetrahydronaphthalen-2-yl]-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-[6-(2-propenyloxy)-tetrahydronaphthalen-2-yl)-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene,-   6-[6-(trans-2-butenyloxy)-tetrahydronaphthalen-2-yl]-2-(trans-2-butenyloxy)-trans-decahydronaphthalene,-   6-[6-(trans-2-butenyloxy)-tetrahydronaphthalen-2-yl]-2-(2-fluoroethenyl)-trans-decahydronaphthalene,-   6-[6-(trans-2-butenyloxy)-tetrahydronaphthalen-2-yl]-2-(2,2-difluoroethenyl)-trans-decahydronaphthalene.

Example 32 Synthesis of2-ethoxy-6-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-trans-decahydronaphthalene

(32-a) Synthesis of2-(3,5-difluorophenyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-6-oneethyleneacetal

To a suspension of 3 g of metal magnesium in 15 ml of THF, a 95 ml THFsolution of 23 g of 3,5-difluoro-1-bromobenzene was added dropwise toobtain a Grignard reagent. A 60 ml THF solution of 21 g oftrans-decahydronaphthalen-2,6-dione monoethyleneacetal was addeddropwise to the reagent while cooling the solution to 10° C. or lower.The temperature was reduced to room temperature, and the mixture wasstirred for 1 hour. After a saturated aqueous solution of ammoniumchloride was added, the organic phase was separated, rinsed with asaturated saline solution, and dried on anhydrous sodium sulfate, andthe solvent was evaporated. The oily substance obtained was dissolved in140 ml of toluene. 4 g of p-toluenesulfonic acid monohydrate was addedto the solution, and the mixture was heated for 4 hours under refluxingusing an apparatus equipped with a water separator until evaporation ofwater stopped. Then, 4 g of p-toluenesulfonic acid monohydrate and 12 gof ethylene glycol was further added, and the mixture was further heatedfor 4 hours under refluxing until evaporation of water stopped. Thesolution was cooled to room temperature. Water was added to thesolution, and the organic phase was separated, rinsed with a saturatedaqueous solution of sodium hydrogencarbonate, water, and a saturatedsaline solution, in sequence, and dried on anhydrous sodium sulfate. Thesolvent was evaporated to obtain 29 g of2-(3,5-difluorophenyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-6-oneethyleneacetal as a pale yellow oily substance.

(32-b) Synthesis of6-(3,5-difluorophenyl)-trans-decahydro-2-naphthalenone ethyleneacetal

29 g of2-(3,5-difluorophenyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-6-oneethyleneacetal, which was obtained in (32-a), was dissolved in 150 ml ofethyl acetate. 6 g of carbon with 5% palladium was added to thesolution, and hydrogenation was carried out for 6 hours at roomtemperature in hydrogen under a pressure of 490 KPa. The catalyst wasseparated by filtration through celite. The solvent was evaporated toobtain 22 g of 6-(3,5-difluorophenyl)-trans-decahydro-2-naphthalenoneethyleneacetal as a pale yellow oily substance.

(32-c) Synthesis of6-(3,5-difluorophenyl)-trans-decahydro-2-naphthalenone

22 g of 6-(3,5-difluorophenyl)-trans-decahydro-2-naphthalenoneethyleneacetal, which was obtained in (32-b), was dissolved in 110 ml oftoluene. 50 ml of formic acid was added to the solution, and the mixturewas stirred for 1 hour at room temperature. Water was added to themixture, and the organic phase was separated and rinsed with water, asaturated aqueous solution of sodium hydrogencarbonate, and a saturatedsaline solution, in sequence, and dried on anhydrous sodium sulfate. Thesolvent was evaporated to obtain 13 g of pale yellow solid6-(3,5-difluorophenyl)-trans-decahydro-2-naphthalenone.

(32-d) Synthesis of6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-ol

13 g of 6-(3,5-difluorophenyl)-trans-decahydro-2-naphthalenone, whichwas obtained in (32-c), was dissolved in 70 ml of methanol. Whilecooling the solution to 10° C. or lower, 2 g of sodium borohydride wasadded in small amounts to the solution. The mixture was stirred for 1hour at room temperature. Water was added to the solution, andextraction was carried out using ethyl acetate. The extracts were rinsedwith water and a saturated saline solution and dried on anhydrous sodiumsulfate, and the solvent was evaporated to obtain 12 g of pale yellowsolid 6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-ol.

(32-e) Synthesis of2-(3,5-difluorophenyl)-6-ethoxy-trans-decahydronaphthalene

To a suspension of 4 g of 60% sodium hydride in 20 ml of DMF, a 60 mlN,N-dimethylformamide (DMF) solution of 12 g of6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-ol, which wasobtained in (32-d), was added dropwise while the mixture was cooled to10° C. or lower. The temperature was reduced to room temperature, andthe mixture was stirred for 30 minutes. Thereafter, a 20 ml DMF solutionof 11 g of ethyl iodide was added dropwise to the mixture while it iscooled to 10° C. or lower. After heating the mixture at 60° C. for 8hours while stirring, water and ethyl acetate were added to the mixture.The organic solution was separated, rinsed with water and a saturatedsaline solution, and dried on anhydrous sodium sulfate. Then, thesolvent was evaporated, and the residue was purified by silica gelcolumn chromatography (hexane) and recrystallized from ethanol to obtain10 g of white solid2-(3,5-difluorophenyl)-6-ethoxy-trans-decahydronaphthalene

(32-f) Synthesis of2-(3,5-difluoro-4-iodophenyl)-6-ethoxy-trans-decahydronaphthalene

To a 50 ml THF solution of 10 g of2-(3,5-difluorophenyl)-6-ethoxy-trans-decahydronaphthalene, which wasobtained in (32-e), the solution being cooled to −70° C., 22 ml of 1.6 Mhexane solution of butyl lithium was added dropwise over a period of 5minutes while maintaining the inner temperature at −50° C. or lower. A40 ml THF solution of 8 g of iodine was added dropwise to the mixtureover a period of 10 minutes. After generation of heat stopped, thetemperature was raised to room temperature, and water and ethyl acetatewere added. The organic phase was separated, rinsed with an aqueoussolution of sodium hydrogen sulfite, water, a saturated aqueous solutionof sodium hydrogencarbonate, water, and a saturated saline solution, insequence, and dried on anhydrous sodium sulfate. The solvent wasevaporated to obtain 13 g of yellow solid2-(3,5-difluoro-4-iodophenyl)-6-ethoxy-trans-decahydronaphthalene.

(32-g) Synthesis of2-ethoxy-6-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-trans-decahydronaphthalene

13 g of-(3,5-difluoro-4-iodophenyl)-6-ethoxy-trans-decahydronaphthalene, whichwas obtained in (32-f), was dissolved in 60 ml of toluene. 1.3 g oftetrakis(triphenylphosphine)palladium(0) and 30 ml of 2M aqueoussolution of sodium carbonate were added, and a 30 ml ethanol solution of8 g of 3,4-difluorophenylboronic acid was further added dropwise over aperiod of 10 minutes. After heating the mixture for 24 hours at 70° C.while stirring, the mixture was cooled to room temperature, and waterwas added to the mixture. After extraction was carried out usingtoluene, the organic phase was rinsed with a saline solution and driedon anhydrous magnesium sulfate. After the solvent was evaporated, theresidue was purified by silica gel column chromatography (hexane) andrecrystallized from ethanol to obtain 4 g white crystals of2-ethoxy-6-(3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-trans-decahydronaphthalene.

The following compounds were prepared in the same manner as mentionedabove:

-   2-vinyl-6-[4-(4-fluorophenyl)phenyl]-trans-decahydronaphthalene,-   2-(trans-1-propenyl)-6-[4-(4-fluorophenyl)phenyl]-trans-decahydronaphthalene,-   2-(3-butenyl)-6-[4-(4-fluorophenyl)phenyl]-trans-decahydronaphthalene,-   2-(trans-3-pentenyl)-6-[4-(4-fluorophenyl)phenyl]-trans-decahydronaphthalene,-   2-ethoxy-6-[4-(4-fluorophenyl)phenyl]-trans-decahydronaphthalene,-   2-vinyl-6-[4-(4-trifluoromethoxyphenyl)phenyl]-trans-decahydronaphthalene.

Example 33 Synthesis of 3-fluoro-4-cyanophenyl4-(6-vinyl-trans-decahydronaphthalen-2-yl)benzoate

(33-a) Synthesis of2-(4-bromophenyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-6-oneethyleneacetal

In a manner similar to that in (1-a), reaction of 17 g ofdecahydronaphthalen-2,6-dione monoethyleneacetal with a Grignard reagentprepared from 4-bromo-1-iodobenzene, dehydration, and re-acetalizationwere carried out to obtain 24 g of pale yellow solid2-(4-bromophenyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-6-oneethyleneacetal.

(33-b) Synthesis of 6-(4-bromophenyl)-trans-decahydro-2-naphthalenoneethyleneacetal

In a manner similar to that in (1-b), catalytic hydrogenation reductionof 24 g of6-(4-bromophenyl)-trans-1,2,3,4,7,8,9,10-octahydro-2-naphthalenoneethyleneacetal, which was obtained in (33-a), was carried out to obtain21 g of pale yellow solid6-(4-bromophenyl)-trans-decahydro-2-naphthalenone ethyleneacetal.

(33-c) Synthesis of 6-(4-bromophenyl)-trans-decahydro-2-naphthalenone

Deacetalization of 21 g of2-(4-bromophenyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-6-oneethyleneacetal, which was obtained in (33-b), was carried out to obtain14 g of pale yellow solid6-(4-bromophenyl)-trans-decahydro-2-naphthalenone.

(33-d) Synthesis of6-(4-bromophenyl)-trans-decahydronaphthalene-2-carbaldehyde

A 70 ml THF solution of 14 g of6-(4-bromophenyl)-trans-decahydro-2-naphthalenone, which was obtained in(33-c), was added dropwise to a Wittig reagent prepared from 19 g ofmethoxymethyltriphenylphosphonium chloride and 7 g of potassiumt-butoxide in 130 ml of THF, while the mixture was cooled to 10° C. orlower. The temperature was reduced to room temperature. After themixture was stirred for 4 hours, water and hexane were added. Theorganic phase was separated and rinsed with water, and the solvent wasevaporated. The pale yellow solid substance obtained was dissolved in 95ml of THF. 80 ml of 10% hydrochloric acid was added, and the mixture washeated for 3 hours under refluxing. The temperature was reduced to roomtemperature, and the organic phase was separated. The aqueous phase wasextracted with ethyl acetate. Organic phases were combined, rinsed witha saturated aqueous solution of sodium hydrogencarbonate, water, and asaturated saline solution, in sequence, and the solvent was evaporated.The pale yellow solid substance was dissolved in 90 ml of methanol.While the solution was cooled to 10° C. or lower, 10 ml of 10% aqueoussolution of sodium hydroxide was added to the solution. After stirringfor 2 hours, the temperature was reduced to room temperature, and thesolvent was evaporated. The pale yellow solid substance obtained wasrinsed with water and recrystallized from a hexane solution to obtain 11g of pale yellow solid6-(4-bromophenyl)-trans-decahydronaphthalene-2-carbaldehyde.

(33-e) Synthesis of 2-(4-bromophenyl)-6-vinyl-trans-decahydronaphthalene

A 60 ml THF solution of 11 g of6-(4-bromophenyl)-trans-decahydronaphthalene-2-carbaldehyde, which wasobtained in (33-d), was added dropwise to a Wittig reagent prepared from14 g of methyltriphenylphosphonium bromide and 5 g of potassiumt-butoxide in 90 ml of THF, while the mixture was cooled to 10° C. orlower. The temperature was reduced to room temperature. After themixture was stirred for 3 hours, water and hexane were added. Theorganic phase was separated and rinsed with water, and the solvent wasevaporated. The residue was purified by silica gel column chromatography(hexane) and recrystallized from ethanol to obtain 9 g of white solid2-(4-bromophenyl)-6-vinyl-trans-decahydronaphthalene.

(33-f) Synthesis of 4-(6-vinyl-trans-decahydronaphthalen-2-yl)benzoicacid

To a suspension of 1 g of metal magnesium in 5 ml of THF, a 40 ml THFsolution of 9 g of 2-(4-bromophenyl)-6-vinyl-trans-decahydronaphthalenewas added dropwise to obtain a Grignard reagent. Carbon dioxide wasinjected into the reagent until saturation while cooling the solution to10° C. or lower. After the mixture was stirred for 1 hour at roomtemperature, 10% hydrochloric acid was added. Then, the organic phasewas separated, rinsed with a saturated saline solution, and dried onanhydrous magnesium sulfate. The solvent was evaporated to obtain 8 g ofmilky-white solid 4-(6-vinyl-trans-decahydronaphthalen-2-yl)benzoicacid.

(33-g) Synthesis of 3-fluoro-4-cyanophenyl4-(6-vinyl-trans-decahydronaphthalen-2-yl)benzoate

8 g of 4-(6-vinyl-trans-decahydronaphthalen-2-yl)benzoic acid, which wasobtained in (33-f), was dissolved in 40 ml of dichloromethane. 8 g ofthionyl chloride, 0.1 ml of pyridine, and 2 ml of DMF were added to thesolution, and the mixture was heated for 1 hour under refluxing. Afterexcessive thionyl chloride and solvent were evaporated, 40 ml ofdichloromethane was added, then 4 g of 3-fluoro-4-cyanophenol and 4 g ofpyridine were added, and the mixture was stirred for 8 hours at roomtemperature. 10% hydrochloric acid was added, and the organic phase wasseparated and rinsed with a saturated aqueous solution of sodiumhydrogencarbonate and a saturated saline solution, in sequence, anddried on anhydrous sodium sulfate. After the solvent was evaporated, theresidue was purified by silica gel chromatography (hexane/ethylacetate), and recrystallized from ethanol to obtain 5 g white crystalsof 3-fluoro-4-cyanophenyl4-(6-vinyl-trans-decahydronaphthalen-2-yl)benzoate.

The following compounds were prepared in the same manner as mentionedabove:

-   4-fluorophenyl 4-(6-vinyl-trans-decahydronaphthalen-2-yl)benzoate,-   4-fluorophenyl    4-[6-(trans-1-propenyl)-trans-decahydronaphthalen-2-yl]benzoate.

Example 34 Synthesis of2-(3-butenyl)-6-[4-(4-methylphenylethynyl)phenyl]-trans-decahydronaphthalene

(34-a) Synthesis of2-(4-bromophenyl)-6-(3-oxopropyl)-trans-decahydronaphthalene

Reaction of 10 g of6-(4-bromophenyl)-trans-decahydronaphthalene-2-carbaldehyde with aWittig reagent and hydrolyzation with acid were carried out to obtain 7g pale yellow crystals of2-(4-bromophenyl)-6-(3-oxopropyl)-trans-decahydronaphthalene.

(34-b) Synthesis of2-(4-bromophenyl)-6-(3-butenyl)-trans-decahydronaphthalene

In a manner similar to that in (2-e), reaction of 7 g of2-(4-bromophenyl)-6-(3-oxopropyl)-trans-decahydronaphthalene was carriedout to obtain 6 g white crystals of2-(4-bromophenyl)-6-(3-butenyl)-trans-decahydronaphthalene.

(34-c) Synthesis of2-(3-butenyl)-6-[4-(4-methylphenylethynyl)phenyl]-trans-decahydronaphthalene

6 g of 2-(4-bromophenyl)-6-(3-butenyl)-trans-decahydronaphthalene, whichwas obtained in (34-b), was dissolved in 30 ml of DMF. 0.8 g oftetrakis(triphenylphosphine)palladium(0), 0.6 g of copper iodide (I),and 2 g of (4-methyl)phenylacetylene were added to the mixture. Afterheating the mixture for 2 hours at 50° C. while stirring, the mixturewas cooled to room temperature, and 10% hydrochloric acid was added tothe mixture. After extraction was carried out using toluene, the organicphase was rinsed with a saline solution and dried on anhydrous magnesiumsulfate. After the solvent was evaporated, the residue was purified bysilica gel column chromatography (hexane) and recrystallized fromethanol to obtain 4 g white crystals of2-(3-butenyl)-6-[4-(4-methylphenylethynyl)phenyl]-trans-decahydronaphthalene.

The following compounds were prepared in the same manner as mentionedabove:

-   2-vinyl-6-[4-(4-fluorophenylethynyl)phenyl]-trans-decahydronaphthalene,-   2-(trans-1-propenyl)-6-[4-(4-fluorophenylethynyl)phenyl]-trans-decahydronaphthalene,-   2-(3-butenyl)-6-[4-(4-fluorophenylethynyl)phenyl]-trans-decahydronaphthalene,-   2-(trans-3-pentenyl)-6-[4-(4-fluorophenylethynyl)phenyl]-trans-decahydronaphthalene,-   2-ethoxy-6-[4-(4-fluorophenylethynyl)phenyl]-trans-decahydronaphthalene,-   2-(trans-1-propenyl)-6-[2,3-difluoro-4-(2,3-difluoro-4-methoxyphenyl)phenyl]-trans-decahydronaphthalene,-   2-ethoxy-6-[2,3-difluoro-4-[2,3-difluoro-4-(trans-2-butenyloxy)phenylethynyl]phenyl]-trans-decahydronaphthalene.

Example 35 Synthesis of6-(4-ethoxy-trans-cyclohexyl)-2-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene

(35-a) Synthesis of4-[2-(3,4,5-trifluorophenyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalen-6-yl]cyclohexanoneethyleneacetal

In a manner similar to that in (1-a), reaction of 15 g of4-(6-oxo-trans-octahydronaphthalen-2-yl)cyclohexanone monoethyleneacetalwith a Grignard reagent prepared from 3,4,5-trifluoro-1-bromobenzene,dehydration, and re-acetalization were carried out to obtain 18 g ofpale yellow solid4-[2-(3,4,5-trifluorophenyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalen-6-yl]cyclohexanoneethyleneacetal.

(35-b) Synthesis of4-[6-(3,4,5-trifluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanonemonoethyleneaceta

In a manner similar to that in (1-b), catalytic hydrogenation reductionof 18 g of4-[2-(3,4,5-trifluorophenyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalen-6-yl]cyclohexanoneethyleneacetal, which was obtained in (35-a), was carried out to obtain16 g of pale yellow solid4-[6-(3,4,5-trifluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanonemonoethyleneacetal.

(35-c) Synthesis of4-[6-(3,4,5-trifluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanone

Deacetalization of 16 g of4-[6-(3,4,5-trifluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanonemonoethyleneacetal, which was obtained in (35-b), was carried out toobtain 11 g of pale yellow solid4-[6-(3,4,5-trifluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanone.

(4-d) Synthesis of2-(4-hydroxy-trans-cyclohexyl)-6-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene

Reduction of 11 g of4-[6-(3,4,5-trifluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanone,which was obtained in (35-c), was carried out to obtain 7 g of paleyellow solid2-(4-hydroxy-trans-cyclohexyl)-6-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene.

(35-e) Synthesis of6-(4-ethoxy-trans-cyclohexyl)-2-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene

Etherification of 7 g of2-(4-hydroxy-trans-cyclohexyl)-6-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene,which was obtained in (35-d), was carried out to obtain 3 g of whitesolid6-(4-ethoxy-trans-cyclohexyl)-2-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene.

The following compounds were prepared in the same manner as mentionedabove:

-   6-(4-ethoxy-trans-cyclohexyl)-2-(4-fluorophenyl)-trans-decahydronaphthalene,-   6-(4-ethoxy-trans-cyclohexyl)-2-(4-trifluoromethoxyphenyl)-trans-decahydronaphthalene.

Example 36 Synthesis of 3,5-difluoro-4-cyanophenyltrans-4-(6-propyl-trans-decahydronaphthalen-2-yl)cyclohexanecarboxylate

(36-a) Synthesis oftrans-4-(6-propyl-trans-decahydronaphthalen-2-yl)cyclohexanecarbaldehyde

Reaction of 10 g of4-(6-propyl-trans-decahydronaphthalen-2-yl)cyclohexanone with a Wittigreagent was carried out to obtain 8 g pale yellow crystals oftrans-4-(6-propyl-trans-decahydronaphthalen-2-yl)cyclohexanecarbaldehyde.

(36-b) Synthesis oftrans-4-(6-propyl-trans-decahydronaphthalen-2-yl)cyclohexanecarboxylicacid flu 8 g oftrans-4-(6-propyl-trans-decahydronaphthalen-2-yl)cyclohexanecarbaldehyde,which was obtained in (36-a), was added dropwise to a 30 ml aqueoussolution of 8 g of concentrated sulfuric acid and 3 g of potassiumpermanganate while the mixture was cooled to 10° C. or lower. Afterstirring the mixture for 30 minutes at room temperature, water and ethylacetate were added. The organic phase was separated and rinsed withwater, a saturated aqueous solution of sodium hydrogencarbonate, water,and a saturated saline solution, in sequence. After the organic phasewas dried on anhydrous sodium sulfate, the solvent was evaporated. Theresidue was recrystallized from a hexane solution to obtain 3 g whitesolidtrans-4-(6-propyl-trans-decahydronaphthalen-2-yl)cyclohexanecarboxylicacid.(36-c) Synthesis of 4-cyano-3,5-difluorophenyltrans-4-(6-propyl-trans-decahydronaphthalen-2-yl)cyclohexanecarboxylate

Esterification reaction of 3 g oftrans-4-(6-propyl-trans-decahydronaphthalen-2-yl)cyclohexanecarboxylicacid, which was obtained in (36-b), with 3,5-difluoro-4-cyanophenol wascarried out to obtain 2 g white crystals of 4-cyano-3,5-difluorophenyltrans-4-[6-propyl-trans-decahydronaphthalen-2-yl]cyclohexanecarboxylate.

The following compounds were prepared in the same manner as mentionedabove:

-   4-fluorophenyl    6-(trans-4-methylcyclohexyl)-trans-decahydronaphthalenecarboxylate,-   4-fluorophenyl    6-(trans-4-ethylcyclohexyl)-trans-decahydronaphthalenecarboxylate,-   3,5-difluoro-4-(trans-2-butenyloxy)phenyl    trans-4-[6-(trans-3-pentenyl)-trans-decahydronaphthalen-2-yl]cyclohexanecarboxylate.

Example 37 Synthesis of6-(trans-4-propylcyclohexyl)-2-(1,2-difluoronaphthalen-6-yl)-trans-decahydronaphthalene

(37-a) Synthesis of6-(1,2-difluoronaphthalen-6-yl)-2-(trans-4-propylcyclohexyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene

In a manner similar to that in (1-a), reaction of 7 g of6-(trans-4-propylcyclohexyl)-trans-decahydronaphthalene with a Grignardreagent prepared from 1,2-difluoro-6-bromonaphthalene and dehydrationwere carried out to obtain 9 g of pale yellow solid6-(1,2-difluoronaphthalen-6-yl)-2-(trans-4-propylcyclohexyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene.

(37-b) Synthesis of6-(trans-4-propylcyclohexyl)-2-(1,2-difluoronaphthalen-6-yl)-decahydronaphthalene

In a manner similar to that in (1-b), catalytic hydrogenation reductionof 9 g of6-(1,2-difluoronaphthalen-6-yl)-2-(trans-4-propylcyclohexyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene,which was obtained in (37-a), was carried out to obtain a 7 g cis/transmixture of pale yellow solid6-(trans-4-propylcyclohexyl)-2-(1,2-difluoronaphthalen-6-yl)-decahydronaphthalene.

(37-c) Isomerization of6-(trans-4-propylcyclohexyl)-2-(1,2-difluoronaphthalen-6-yl)-decahydronaphthalene

7 g cis/trans mixture of6-(trans-4-propylcyclohexyl)-2-(1,2-difluoronaphthalen-6-yl)-decahydronaphthalene,which was obtained in (37-b), was dissolved in 40 ml of DMF. While thesolution was cooled to 0° C., 2 g of potassium t-butoxide was added tothe solution, and the mixture was stirred for 2 hours. After water andhexane were added to the mixture, the organic phase was separated andrinsed with water and a saturated saline solution, in sequence, anddried on anhydrous magnesium sulfate. Then, the solvent was evaporated.The residue was purified by silica gel column chromatography (hexane)and recrystallized from ethanol to obtain 3 g of white solid6-(trans-4-propylcyclohexyl)-2-(1,2-difluoronaphthalen-6-yl)-decahydronaphthalene.

The following compounds were prepared in the same manner as mentionedabove:

-   6-(trans-4-methylcyclohexyl)-2-(2-fluoronaphthalen-6-yl)-trans-decahydronaphthalene,-   6-(trans-4-ethylcyclohexyl)-2-(2-fluoronaphthalen-6-yl)-trans-decahydronaphthalene,-   6-(trans-4-propylcyclohexyl)-2-(2-fluoronaphthalen-6-yl)-trans-decahydronaphthalene.

Example 38 Preparation of Liquid Crystal Composition (1)

The versatile host liquid crystal (H-A):

was prepared. This host liquid crystal (H-A) exhibits a nematic phase at116.7° C. or less, and its melting point is 11° C. The physical propertyvalues at 20° C. of the threshold voltage (Vth) of a TN cell (cellthickness: 6 μm) prepared using this composition were as shown below.

-   -   Threshold voltage (Vth): 2.14 V    -   Dielectric anisotropy (Δε): 4.8    -   Birefringence (Δn): 0.090

Next, when a liquid crystal composition (H-1) was prepared comprised of80% of this host liquid crystal (H-A) and 20% of compound (I-3):

of the present invention obtained in Example 1, the upper limittemperature of the nematic phase was 88.7° C., which was slightly lowerthan that of the host liquid crystal (H-A). This composition was notobserved to exhibit crystal precipitation or phase separation even whenallowed to stand for 1 month or more at 0° C., indicating that compound(I-3) of the present invention has excellent co-solubility withversatile liquid crystal. Next, when its melting point was measured bycooling to −60° C. and crystallizing, it was determined to be +13° C.,which is roughly equal to that of the host liquid crystal (H-A). Next,when a liquid crystal device was prepared in the same manner using thiscomposition and its physical property values were measured, thefollowing results were obtained.

-   -   T_(N-I): 88.7° C.    -   T_(C-N): 13° C.    -   Threshold voltage (Vth): 1.69 V    -   Dielectric anisotropy (Δε): 5.7    -   Response time (Σr=Σd) 31.0 msec    -   Birefringence (Δn): 0.080

Thus, by adding 20% of the compound of (I-3) of the present invention tohost liquid crystal (H-A), its threshold voltage (Vth) was able to belowered 0.45 V while suppressing the drop in nematic phase upper limittemperature (T_(N-I)) to 28° C. Moreover, the increase in its responsetime was able to be held to less than 6 msec. In addition, the meltingpoint determined by cooling and crystallizing was 13° C., which was onlyslightly different from that of the host liquid crystal (H-A),indicating that (I-3) dissolves easily in the host liquid crystal. Inaddition, the nematic phase upper limit temperature of (I-3) alone asextrapolated from the nematic phase upper limit temperature (T_(N-I)) of(H-1) was −23° C.

Next, although the voltage holding rates of this element at roomtemperature and 80° C. were measured, both were extremely favorable,indicating that this element can be adequately used for active matrixdriving.

Comparative Example 1

Comparative liquid crystal composition (HR-1) was prepared comprised of20% of cyclohexylbenzene derivative (R-1):

used in place of (I-3) in Example 1, and 80% of host liquid crystal(H-A). The nematic phase upper limit temperature (T_(N-I)) of thiscomposition decreased considerably to 70° C. The nematic phase upperlimit temperature of (R-1) alone as extrapolated from this was −100° C.or below. Thus, liquid crystallinity is considerably lower than (I-3).

The physical property values of this composition along with thephotoelectric property values of an element prepared in the same mannerare as shown below.

-   -   Threshold voltage (Vth): 1.58 V    -   Dielectric anisotropy (Δε): 5.6    -   Response time (τr=τd): 30.0 msec    -   Birefringence (Δn): 0.080

Thus, in comparison with (H-1), which is a composition containing thecompound of (I-3) pertaining to the present invention, not only is thenematic phase upper limit temperature (T_(N-I)) nearly 20° C. lower, butthe threshold voltage (Vth) is only decreased by about 0.1 V, andresponse time is essentially unchanged.

Example 39 Preparation of Liquid Crystal Composition (2)

Liquid crystal composition (H-2) was prepared comprised of 20 wt % of(I-18) in Table 3, which is a compound of the present invention:

and 80 wt % of host liquid crystal (H-A). The physical property valuesof (H-2) and the photoelectric characteristic values of a liquid crystaldevice prepared in the same manner using (H-2) were as shown below.

-   -   T_(N-I): 122.8° C.    -   T_(C-N): 2° C.    -   Threshold voltage (Vth): 1.97 V    -   Dielectric anisotropy (Δε): 4.8    -   Response time (τr=τd): 41.3 msec    -   Birefringence (Δn): 0.088

Thus, by adding 20% of (I-18), the nematic phase upper limit temperature(T_(N-I)) was increased 6.1° C., melting point (T_(C-N)) was lowered 9°C., and nematic phase temperature range was increased 15.1° C. Moreover,threshold voltage (Vth) was also able to be decreased 0.17 V. Inaddition, although this (H-2) was allowed to stand for 2 hours at −20°C., crystal precipitation or phase separation was not observed.

Next, although the voltage holding rates of this element at roomtemperature and 80° C. were measured, both were extremely favorable,indicating that this element can be adequately used for active matrixdriving.

Comparative Example 2

A comparative liquid crystal composition (HR-2) was prepared comprisedof 20 wt % of phenylbicyclohexane derivative (R-2):

which, although having a similar structure to (I-18), thetrans-decahydronaphthalene group is substituted with acyclohexane-4,4′-diyl group, and 80 wt % of host liquid crystal (H-A).The physical property values of this composition along with thephotoelectric characteristic values of an element prepared in the samemanner are as shown below.

-   -   T_(N-I): 111.0° C.    -   T_(C-N): +25° C.    -   Threshold voltage (Vth): 2.00 V    -   Dielectric anisotropy (Δε): 5.9    -   Response time (τr=τd): 37.8 msec    -   Birefringence (Δn): 0.087

Thus, in comparison with the case of (H-2), the nematic phase upperlimit temperature (T_(N-I)) dropped by nearly 11.8° C., and thethreshold voltage (Vth) conversely became 0.03 V higher than (H-2)pertaining to the present invention.

Moreover, melting point also rose 13° C. higher than the host liquidcrystal, indicating that the solubility of the compound of (R-2)relative to the host liquid crystal is not that good.

As has been described above, it was determined that the compound of(I-18) of the present invention has effects that are superior to thoseof compounds of the prior art in terms of preparing a liquid crystalcomposition that has a wide temperature range, low threshold voltage andallows high-speed response.

Example 40 Preparation of Liquid Crystal Composition (3)

Versatile n type host liquid crystal (H-B):

was prepared. This (H-B) exhibits a nematic phase at 72.5° C. or less,and its melting point is 17° C. The physical property values of thiscomposition were as shown below.

-   -   Dielectric anisotropy (Δε): −1.3    -   Birefringence (Δn): 0.085

A liquid crystal composition (H-3) was prepared comprised of 80% of hostliquid crystal (H-B) and 20% of compound (I-9):

obtained in Example 10. Its physical property values and photoelectriccharacteristic values measured with a liquid crystal device prepared inthe same manner were as shown below.

-   -   Nematic phase upper limit temperature (T_(N-I)): 76.5° C.    -   Dielectric anisotropy (Δε): 3.2    -   Threshold voltage (Vth): 2.30 V    -   Response time (τ): 40.0 msec    -   Birefringence (Δn): 0.085

Thus, although the threshold voltage (Vth) is a little higher ascompared with (H-B), the nematic phase upper limit temperature is morethan 10° C. higher, and response is also improved, although onlyslightly. In addition, although this (H-3) was allowed to stand for 2weeks at −20° C., liquid crystal precipitation or phase separation wasnot observed.

Comparative Example 3

Nematic liquid crystal composition (H-R³) was prepared by adding 20% of3-fluoro-4-cyanobenzene derivative (R-3):

having a structure in place of (I-9) in Example 40 in which thetrans-decahydronaphthalene group is substituted with a cyclohexylenegroup, to (H-B). The physical property values of this composition alongwith the photoelectric characteristic values of an element prepared inthe same manner are as shown below.

-   -   Nematic phase upper limit temperature (T_(N-I)): 58.5° C.    -   Dielectric anisotropy (Δε): 3.6    -   Threshold voltage (Vth): 2.2 V    -   Response time (r): 36.0 msec    -   Birefringence (Δn): 0.084

It can be seen that Δε of (H-R³) has increased and Vth has beendecreased more effectively. In addition, the response is also fasterthan (H-B). However, T_(N-I) has decreased by nearly 20° C. as comparedwith (H-3). Thus, it can be seen that it is difficult to prepare aliquid crystal composition having both low voltage driving and a widetemperature range with a phenylcyclohexane derivative like (R-3).

Example 41 Preparation of Liquid Crystal Composition (4)

Liquid crystal composition (H-4) was prepared comprised of 80 wt % of(H-A) and 20 wt % of compound (I-23) of the present invention obtainedin Example 22:

The T_(N-I) of this composition was 116.4° C. Although this (H-4) wasallowed to stand for 4 weeks at −20° C., crystal precipitation or phaseseparation was not observed. In addition, when this composition wascrystallized by allowing to stand after cooling to −60° C. followed bymeasurement of T_(C-N), it was found to be −3° C., indicating that itcan be made to be significantly lower than (H-A), and that (I-23)dissolves easily in the host liquid crystal.

Next, (H-4) was filled into a TN cell having a cell thickness of 6.0 μmto prepare a liquid crystal device. Measurement of its photoelectriccharacteristics at 20° C. yielded the values indicated below.

-   -   Threshold voltage (Vth): 2.31 V    -   Response time (τ): 27.4 msec    -   Sharpness (γ): 1.29    -   Dielectric anisotropy (Δε): 3.2    -   Birefringence (Δn): 0.081

The value of Δn was able to be lowered while holding the decrease inT_(N-I) to 4° C. by adding 20 wt % of (I-23). In addition, there arehardly any changes in Vth and γ, and the increase in τ was able to beheld to roughly 5 msec.

In addition, although the voltage holding rates of this element at roomtemperature and 80° C. were measured, both were extremely favorable,indicating that this element can be adequately used for active matrixdriving.

Comparative Example 4

Nematic liquid crystal composition (H-R⁴) was prepared by adding thesame amount (20 wt %) of compound (R-4):

in place of (I-23) in Example 41, which although having a similarstructure, has a trans-1,4-cyclohexylene group for the ring structurethat composes the core, to (H-A). A liquid crystal device was preparedin the same manner, and the photoelectric characteristic values of thiscomposition were as shown below.

-   -   Nematic phase upper limit temperature (T_(N-I)): 102.8° C.    -   Melting point (T_(C-N)): --    -   Threshold voltage (Vth): 2.29 V    -   Response time (r): 22.4 msec    -   Sharpness (γ): 1.21    -   Dielectric anisotropy (Δε): 3.6    -   Birefringence (Δn): 0.089

(H-R⁴) has a lower value of T_(N-I) than (H-4) and a narrower nematicphase temperature range. The Δn of (H-R⁴) is larger than (H-4), Δε, Vthand γ are essentially no different from (H-4), and response is betterthan (H-4).

Example 42 Preparation of Liquid Crystal Composition (5)

Liquid crystal composition (M) was prepared composed of the componentslisted below.

-   -   4 wt % of 4-ethoxy-1-(trans-4-propylcyclohexyl)benzene    -   3 wt % of trans-4-pentylcyclohexylcarboxylate-4-methylphenyl    -   3 wt % of trans-4-propylcyclohexanecarboxylate-4-ethoxyphenyl    -   3 wt % of trans-4-(4-methylphenyl)-trans-4′-vinylbicyclohexane    -   3 wt % of trans-4-butyl-trans-4′-propylbicyclohexane    -   4 wt % of trans-4-pentyl-trans-4′-vinylbicyclohexane    -   3 wt % of 4,4-bis(3-butenyl)bicyclohexane    -   4 wt % of 1-(4-propylphenyl)-2-(4-methylphenyl)ethine    -   3 wt % of 1-(4-ethoxyphenyl)-2-(4-pentylphenyl)ethine    -   3 wt % of 1,2-bis[4-(3-butenyl)phenyl]ethine    -   4 wt % of        1-(4-ethylphenyl)ethynyl-4-(trans-4-propylcyclohexyl)benzene    -   3 wt % of 4-(trans-pentylcyclohexyl)-4′-ethylbiphenyl    -   3 wt % of 4-(trans-4-propylcyclohexyl)-1-cyanobenzene    -   4 wt % of        4-[trans-4-(trans-1-propenyl)cyclohexyl]-1-cyanobenzene    -   3 wt % of 4-[trans-4-(3-butenyl)cyclohexyl]-1-cyanobenzene    -   3 wt % of 4-pentyl-4-cyanobiphenyl    -   4 wt % of 2-(4-cyanophenyl)-5-pentylpyrimidine    -   3 wt % of 4-ethylbenzoate-4-cyanophenyl    -   3 wt % of trans-4-pentylcyclohexanecarboxylate-3,4-difluorphenyl    -   4 wt % of 4-butylbenzoate-3-fluoro-4-cyanophenyl    -   3 wt % of        4-(trans-3-penten-1-yl)benzoate-3,5-difluoro-4-cyanophenyl    -   3 wt % of        trans-4-(3-fluoro-4-cyanophenyl)-trans-4′-(3-methoxypropyl)bicyclohexane    -   3 wt % of        trans-4-(3,4-difluorophenyl)-trans-4′-ethylbicyclohexane    -   4 wt % of        trans-4-(3,4-difluorophenyl)-trans-4′-vinylbicyclohexane    -   4 wt % of        trans-4-(3,4,5-trifluorophenyl)-trans-4′-propylbicyclohexane    -   3 wt % of        trans-4-[2-(3,4,5-trifluorophenyl)ethyl]-trans-4-propylbicyclohexane    -   3 wt % of 4-(trans-4-propylcyclohexyl)-4′-cyanobiphenyl    -   4 wt % of        4-(trans-4-propylcyclohexyl)benzoate-3-fluoro-4-cyanophenyl    -   3 wt % of 4-(trans-4-propylcyclohexyl)-3,4,5-trifluorobiphenyl    -   3 wt % of        1-(3,4,5-trifluorophenyl)ethynyl-4-(trans-4-propylcyclohexyl)benzene

The T_(N-I) of this (M) was 75° C., and Δn was 0.142. Liquid crystalcomposition (M-I) was prepared comprised of 3% of (I-10):

obtained in Example 9, 3% of (I-9):

obtained in Example 10, and 4% of (I-3):

obtained in Example 1. The T_(N-I) of this (M-I) was 70.4° C., and Δnwas 0.136.

INDUSTRIAL APPLICABILITY

The novel decahydronaphthalene derivative of the present invention canbe produced industrially extremely easily as shown in the examples, andby adding a small amount to a base liquid crystal, it is possible tohave effects that expand the nematic phase temperature range, therebyimproving its various characteristics as a nematic liquid crystal.Moreover, the novel decahydronaphthalene derivative of the presentinvention also has superior co-solubility with base liquid crystalsgenerally used at present. Thus, it is suitable for various types ofliquid crystal devices requiring a wide operating temperature range, andis extremely useful as a liquid crystal material.

1. A compound represented by general formula (I):

(wherein, R and Z may be substituted with a halogen and represent alkylgroups or alkoxy groups having 1-16 carbon atoms, alkenyl groups having2-16 carbon atoms, alkenyloxy groups having 3-16 carbon atoms, alkylgroups having 1-12 carbon atoms substituted with an alkoxy group having1-10 carbon atoms, hydrogen atoms, fluorine atoms, chlorine atoms,trifluoromethoxy groups, difluoromethoxy groups, trifluoromethyl groups,2,2,2-trifluoroethoxy groups, cyano groups, cyanato groups, hydroxygroups or carboxy groups, m and n may be the same or different andrespectively and independently represent an integer of 0-2, 1≦m+n≦3, Land M may be the same or different and respectively and independentlyrepresent —CH₂CH₂—, —CH(CH₃)CH₂—, —CH₂CH(CH₃)₃—, —CH₂O—, —OCH₂—, —CF₂O—,—OCF₂—, —COO—, —OCO—, —CH═CH—, —CF═CF—, —C≡C—, —O(CH₂)₃—, —(CH₂)₃O—,—(CH₂)₄— or a single bond, rings A and B when present may be the same ordifferent and respectively and independently represent atrans-1,4-cyclohexylene group in which one CH₂ group or more than onenon-adjacent CH₂ groups in the group may be replaced by —O— or —S—, a1,4-phenylene group in which one CH₂ group or more than one non-adjacentCH₂ groups in the group maybe replaced by —N═, a 1,4-cyclohexenylenegroup, 1,4-bicyclo(2,2,2)octylene group, piperidine-1,4-diyl group,naphthalene-2,6-diyl group, trans-decahydronaphthalene-trans-2,6-diylgroup or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and althoughthese may be substituted with a cyano group or halogen, in the case m orn represents 2, at least one of the two L or M present represents asingle bond; provided that the following cases are excluded: i. case inwhich either m or n represents 1, the other of m or n represents 0, ringA or ring B when present represents a 1,4-cyclohexylene group, L or Mwhen present represents a single bond, R or Z bonded to adecahydronaphthalene ring represents a non-substituted alkyl group, andR or Z bonded to a 1,4-cyclohexylene group represents a non-substitutedalkyl group, alkoxy group or alkenyloxy group; ii. case in which eitherm or n represents 1, the other m or n represents 0, ring A or ring Bwhen present represents a 1,4-cyclohexylene group, L when presentrepresents —OCO— or M when present represents —COO—, and R or Z bondedto a 1,4-cyclohexylene group represents a non-substituted alkyl group orcyano group; iii. case in which either m or n represents 1, the other mor n represents 0, ring A or ring B when present represents anon-substituted 1,4-phenylene group, L when present represents —OCO— orM when present represents —COO—, L or M when present represents a singlebond, and R or Z bonded to a 1,4-phenylene group represents anon-substituted alkyl group, alkoxy group, hydroxyl group, hydrogenatom, carboxyl group or cyano group; iv. case in which either m or nrepresents 1, the other m or n represents 0, ring A or ring B whenpresent represent a non-substituted 1,4-phenylene group, L or M whenpresent represents a single bond, R or Z bonded to adecahydronaphthalene ring represents a non-substituted alkoxy group, andR or Z bonded to a 1,4-phenylene group represents a non-substitutedalkyl group; v. case in which either m or n represents 1, the other m orn represents 0, ring A or ring B when present represents atrans-decahydronaphthalene-trans-2,6-diyl group, L when presentrepresents —OCO—, M when present represents —COO— or L or M when presentrepresent a single bond, and R and Z represent non-substituted alkoxygroups; vi. case in which either m or n represents 1, the other m or nrepresents 0, ring A or ring B when present represents a non-substitutednaphthalene-2,6-diyl group, L when present represents —OCO— or M whenpresent represents —COO—, R or Z bonded to a decahydronaphthalene ringrepresents a non-substituted alkyl group, and R or Z bonded to anaphthalene-2,6-diyl group represents anon-substituted alkyl group,bromine atom or cyano group, or the case in which R or Z bonded to adecahydronaphthalene ring represents a non-substituted alkoxy group, andR or Z bonded to a naphthalene-2,6-diyl group represents anon-substituted alkyl group or cyano group; vii. case in which nrepresents 2, m represents 0, R represents a non-substituted alkylgroup, M when present adjacent to a decahydronaphthalene ring represents—COO—, at least one of rings B present represents a non-substituted1,4-phenylene group, and Z resents a non-substituted alkyl group orbromine atom, or the case in which at least one of rings B presentrepresents a pyrimidine-2,5-diyl group, and Z represents anon-substituted alkyl group, alkoxy group or cyano group; and viii. casein which m and n represent 1, ring A represents atrans-decahydronaphthalene-trans-2,6-diyl group or a 1,4-cyclohexylenegroup, ring B represents a non-substituted 1,4-phenylene group or1,4-cyclohexylene group, L represents a single bond, M represents —COO—,—OCO—, —CH₂O or —OCH₂—, and R and Z represent non-substituted alkylgroups.
 2. A compound according to claim 1 wherein, ring A and ring Bwhen present respectively and independently represent a 1,4-phenylenegroup, naphthalene-2,6-diyl group,1,2,3,4-tetrahydronaphthalene-2,6-diyl group, trans-1,4-cyclohexylenegroup or decahydronaphthalene-2,6-diyl group that may be substitutedwith fluorine atom(s).
 3. A compound acing to claim 1 wherein, ring A orring B when present respectively and independently represent a1,4-phenylene group or trans-1,4-cyclohexylene group that may besubstituted with fluorine atom(s).
 4. A compound according to claim 1wherein, L and M when present represent —CH₂CH₂—, —CH₂O—, —OCH₂—,—CF₂O—, —OCF₂—, —COO—, —OCO—, —CF═CF— or a single bond.
 5. A compoundaccording to claim 1 wherein, L or M represents a single bond.
 6. Acompound according to claim 1 wherein, L and M represent single bonds.7. A compound according to claim 1 wherein, 1≦m+n≦2.
 8. A compoundaccording to claim 1 wherein, R represents an alkyl group, alkoxy group,alkenyl group or alkenyloxy group having 1-12 carbon atoms.
 9. Acompound according to claim 1 wherein, Z represents a halogen atom or analkyl group, alkoxy group, alkenyl group, alkenyloxy group or cyanogroup having 1-12 carbon atoms.
 10. A compound according to claim 1wherein, R represents an alkyl group or alkenyl group having 1-12 carbonatoms, m represents 1, n represents 1, ring A represents atrans-1,4-cyclohexylene group, ring B represents a 3-fluoro1,4-phenylene group or 3,5-difluoro-1,4-phenylene group, L and Mrepresent single bonds, and Z represents a fluorine atom, chlorine atom,trifluoromethoxy group, difluoromethoxy group, trifluoromethyl group,2,2,2-trifluoroethoxy group or cyano group.
 11. A compound according toclaim 1 wherein, R represents an alkyl group or alkenyl group having1-12 carbon atoms, m represents 0, n represents 1, ring B represents a3-fluoro 1,4-phenylene group or 3,5-difluoro-1,4-phenylene group, Mrepresents a single bond and Z represents a fluorine atom, chlorineatom, trifluoromethoxy group, difluoromethoxy group, trifluoromethylgroup, 2,2,2-trifluoroethyoxy group or cyano group.
 12. A compoundaccording to claim 1 wherein, R and Z represent alkyl groups or alkenylgroups having 1-12 carbon atoms, m and n represent 1, rings A and Brepresent 1,4-phenylene groups or trans-1,4-cyclohexylene groups, and Land M represent single bonds.
 13. A compound according to claim 1wherein, R and Z represent alkyl groups or alkenyl groups having 1-12carbon atoms, at least one of R or Z represents an alkenyl group, mrepresents 1, n represents 0, rings A and B represent 1,4-phenylenegroups or trans-1,4-cyclohexylene groups, and L represents a singlebond.
 14. A compound represented by general formula (II):

(wherein, R⁴ represents an alkyl group, alkyoxy group, alkenyl group,alkenyloxy group or alkoxyalkyl group, L¹ represents —CH₂CH₂—,—CH(CH₃)CH₂—, —CH₂CH(CH₃)—, —CH₂O—, —OCH₂—, —CF₂O—, —OCF₂—, —COO—,—OCO—, —CH═CH—, —CF═CF—, —C≡C—, —O(CH₂)₃—, —(CH₂)₃O—, —(CH₂)₄—, or asingle bond, R⁴ represents an alkenyl group, alkenyloxy group oralkyoxyalkyl group when L¹ presents a single bond, ring A represents atrans-1,4 cyclohexylene group in which one CH₂ group or more than onenon-adjacent CH₂ groups in the group may be replaced by —O— or —S—, a1,4-phenylene group in which one CH₂ group or more than one non-adjacentCH₂ groups in the group may be replaced by —N═, a 1,4-cyclohexenylenegroup, 1,4-bicyclo(2,2,2)octylene group, piperidine-1,4-diyl group,naphthalene-2,6-diyl group, trans-decahydronaphthalene-trans-2,6-diylgroup or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, m represents aninteger of 1 or 2, and the decahydronaphthalene ring has a trans form).15. A production method of general formula (II) according to claim 14including: reducing a compound represented by general formula (II-A):

(wherein, R⁴ is the same as previously defined in general formula (II),ring E represents a 1,4-phenyl group or trans-1,4-cyclohexylene group, Lis the same as L¹ defined in general formula (II), and m is the same aspreviously defined in general formula (II), and the decahydronaphthalenering has a trans form), and oxidizing the hydroxyl group as necessary.16. A compound represented by general formula (V-2):

(wherein, U¹ and U² respectively and independently represent an oxygenatom or the following structure:

(wherein, k represents an integer from 1 to 7), L represents —CH₂CH₂—,—CH(CH₃)CH₂—, —CH₂CH(CH₃)—, —CH₂O—, —OCH₂—, —CF₂O—, —OCF₂—, —COO—,—OCO—, —CH═CH—, —CF═CF—, —C≡C—, —O(CH₂)₃—, —(CH₂)₃O—, —(CH₂)₄— or asingle bond, and the decahydronaphthalene ring has a trans form).
 17. Aproduction method of general formula (V-2) according to claim 16,including: converting a compound represented by general formula (V-2A):

(wherein, k and L are the same as previously defined in claim 16) intoan enamine using a secondary amine, and reacting it with methyl vinylketone to obtain a compound represented by general formula (V-2B)

as previously defined in claim 16) followed by reductive hydrogenation.18. A production method of general formula (V-2) according to claim 16represented by general formula (V-2C):

(wherein, although ring G represents a cyclohexane ring or benzene ring,a single bond(s) of the cyclohexane ring may be replaced by doublebond(s), and although rings F and H respectively and independentlyrepresent the following structures:

a single bond(s) of the cyclohexane ring may be replaced by doublebond(s)), oxidizing the hydroxyl group as necessary, and furtherprotecting the carbonyl group as necessary.
 19. A production method ofgeneral formula (V-1a):

(wherein k represents an integer from 1 to 7) including monoacetalationof a compound represented by general formula (V-1D):


20. A liquid crystal composition containing a compound according toclaim
 1. 21. A liquid crystal device having for its constituent featurethe liquid crystal composition according to claim
 20. 22. An activematrix drive, liquid crystal device that uses the liquid crystalcomposition according to claim
 20. 23. A super twisted nematic liquidcrystal device that uses the liquid crystal composition according toclaim 21.